tretinoin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
retinol derivatives 2722 302-79-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • tretinoin potassium
  • trans-Retinoic acid
  • tretinoin sodium
  • retinoic acid
  • tretinoin
An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).
  • Molecular weight: 300.44
  • Formula: C20H28O2
  • CLOGP: 6.74
  • LIPINSKI: 1
  • HAC: 2
  • HDO: 1
  • TPSA: 37.30
  • ALOGS: -4.80
  • ROTB: 5
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 3.70 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 50 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 3.481 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.897 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 8.670 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 37.068 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 0.130 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 0.270 % High 1
herg hERG pIC50 4.709 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 46.881 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 11.429 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 0.370 % High 1
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2D,CDK5,CDK9,DYRK1B,EGFR,EIF2AK3,ERBB2,GRK2,GSK3B,IKBKB,ITK,MAP2K6,MAP3K7,MAPK7,MAPKAPK2,PDK1,PDK2,PDK4,PIK3CB,PRKDC,STK33,SYK,TEK,TGFBR1 30
kinase-selectivity-class ACVR2B,AXL,BRAF,EIF2AK3,EPHB4,GRK2,MAP2K6,MAPK7,STK33,TEK,TTK 11
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.722 High 1
mh-clint Mouse hepatocyte intrinsic clearance 44.157 High 1
mppb Mouse plasma protein binding (% unbound) 0.150 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 3.622 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 0.110 % High 1
rh-clint Rat hepatocyte intrinsic clearance 26.915 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 5.680 % High 1
rppb Rat plasma protein binding (% unbound) 0.120 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 80.724 uM High 1

Approvals:

DateAgencyCompanyOrphan
Oct. 20, 1971 FDA VALEANT INTL

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Differentiation syndrome 839.53 15.39 165 25476 1166 90601640
Taste disorder 384.49 15.39 231 25410 61315 90541491
Blepharospasm 348.63 15.39 209 25432 55236 90547570
Epilepsy 291.61 15.39 217 25424 81989 90520817
Gastrooesophageal reflux disease 168.48 15.39 221 25420 166116 90436690
Overlap syndrome 161.38 15.39 68 25573 8480 90594326
Onychomadesis 144.44 15.39 113 25528 45885 90556921
Infusion site reaction 141.34 15.39 80 25561 18959 90583847
Product use in unapproved indication 139.36 15.39 299 25342 335937 90266869
Product quality issue 139.01 15.39 140 25501 79185 90523621
Back injury 138.81 15.39 111 25530 46511 90556295
Memory impairment 127.24 15.39 212 25429 197032 90405774
Paraesthesia 119.42 15.39 236 25405 250090 90352716
Idiopathic intracranial hypertension 119.22 15.39 43 25598 3538 90599268
Neck pain 102.49 15.39 143 25498 113820 90488986
Breast cancer stage III 91.34 15.39 116 25525 84331 90518475
Migraine 90.13 15.39 179 25462 190213 90412593
Intracranial pressure increased 89.39 15.39 42 25599 6769 90596037
Hypoaesthesia 87.70 15.39 240 25401 313970 90288836
Peripheral venous disease 85.63 15.39 112 25529 83809 90518997
Live birth 81.37 15.39 106 25535 79001 90523805
Abdominal pain upper 81.08 15.39 242 25399 332432 90270374
Nail disorder 78.35 15.39 90 25551 58977 90543829
Maternal exposure during pregnancy 68.77 15.39 241 25400 359822 90242984
Night sweats 62.02 15.39 122 25519 128644 90474162
Leukaemia recurrent 57.92 15.39 20 25621 1447 90601359
Lip dry 57.78 15.39 103 25538 100852 90501954
Fatigue 55.11 15.39 157 25484 1153866 89448940
Liver function test increased 54.35 15.39 91 25550 84764 90518042
Facet joint syndrome 53.28 15.39 98 25543 98291 90504515
Bursitis 52.01 15.39 115 25526 131539 90471267
Wound infection 50.25 15.39 100 25541 106302 90496504
Osteoarthritis 49.14 15.39 144 25497 195586 90407220
Drug intolerance 46.29 15.39 249 25392 447342 90155464
Rheumatic fever 44.68 15.39 119 25522 153002 90449804
Hypercholesterolaemia 44.29 15.39 92 25549 100800 90502006
Therapeutic product effect incomplete 42.46 15.39 136 25505 193760 90409046
Dyspnoea 41.13 15.39 121 25520 880834 89721972
Obesity 40.36 15.39 91 25550 105416 90497390
Dermatitis atopic 40.30 15.39 41 25600 23431 90579375
Product administration interrupted 39.87 15.39 31 25610 12461 90590345
Toxicity to various agents 39.49 15.39 16 25625 287830 90314976
Normal newborn 38.65 15.39 40 25601 23322 90579484
Haematopoietic neoplasm 37.34 15.39 7 25634 37 90602769
Inflammation 36.17 15.39 122 25519 178470 90424336
Sleep disorder 35.55 15.39 130 25511 197900 90404906
Dysphoria 35.55 15.39 22 25619 6132 90596674
Psoriatic arthropathy 34.56 15.39 142 25499 228193 90374613
Urinary tract infection 34.44 15.39 22 25619 305610 90297196
Cough 33.49 15.39 33 25608 368929 90233877
Fall 33.38 15.39 53 25588 481757 90121049
Gait inability 32.30 15.39 103 25538 146353 90456453
Joint range of motion decreased 31.39 15.39 97 25544 135546 90467260
Skin warm 31.09 15.39 22 25619 7665 90595141
Dry mouth 30.68 15.39 118 25523 183941 90418865
Acne 30.55 15.39 39 25602 28468 90574338
Musculoskeletal pain 30.38 15.39 112 25529 171139 90431667
Completed suicide 30.22 15.39 3 25638 145055 90457751
Haemorrhagic diathesis 30.03 15.39 19 25622 5505 90597301
Bone marrow necrosis 29.41 15.39 7 25634 130 90602676
Lower respiratory tract infection fungal 29.17 15.39 8 25633 266 90602540
Death 29.07 15.39 53 25588 456498 90146308
Depression 28.86 15.39 164 25477 300437 90302369
Injury 28.50 15.39 121 25520 197228 90405578
Xerosis 28.45 15.39 12 25629 1499 90601307
Malaise 28.38 15.39 79 25562 585907 90016899
Polyarteritis nodosa 27.75 15.39 8 25633 320 90602486
Lung disorder 27.40 15.39 99 25542 149784 90453022
Dry skin 26.23 15.39 69 25572 88004 90514802
Blood cholesterol increased 25.87 15.39 122 25519 207890 90394916
Abortion spontaneous 25.74 15.39 51 25590 54005 90548801
Appetite disorder 25.59 15.39 21 25620 9112 90593694
Acute myeloid leukaemia 24.95 15.39 30 25611 20610 90582196
Hyponatraemia 24.82 15.39 4 25637 133534 90469272
Dehydration 24.78 15.39 12 25629 194435 90408371
Type 2 diabetes mellitus 24.40 15.39 118 25523 203126 90399680
Muscular weakness 24.10 15.39 119 25522 206547 90396259
Blister 23.73 15.39 138 25503 254860 90347946
Acute kidney injury 23.37 15.39 34 25607 320353 90282453
Papilloedema 22.93 15.39 15 25626 4600 90598206
Breast cancer stage II 22.75 15.39 38 25603 35296 90567510
Folliculitis 22.66 15.39 116 25525 204237 90398569
C-reactive protein increased 22.27 15.39 106 25535 181283 90421523
Arthritis infective 21.61 15.39 18 25623 7974 90594832
Myelodysplastic syndrome 21.46 15.39 28 25613 20875 90581931
Muscle injury 20.80 15.39 102 25539 176552 90426254
Hypocholesterolaemia 20.57 15.39 16 25625 6433 90596373
Hypotension 20.49 15.39 38 25603 325359 90277447
Chloroma 20.48 15.39 6 25635 254 90602552
Muscle spasms 20.09 15.39 131 25510 251752 90351054
Intentional product use issue 19.93 15.39 117 25524 216775 90386031
VIth nerve paralysis 19.85 15.39 8 25633 890 90601916
Product label confusion 19.52 15.39 28 25613 22822 90579984
Pericarditis 19.45 15.39 137 25504 270014 90332792
Disease progression 19.45 15.39 10 25631 156605 90446201
Pyrexia 19.23 15.39 109 25532 660376 89942430
Product use issue 18.58 15.39 158 25483 329761 90273045
Chloasma 18.51 15.39 5 25636 157 90602649
Oesophageal mass 18.29 15.39 4 25637 50 90602756
Fibromyalgia 18.14 15.39 110 25531 206159 90396647
Application site dryness 18.07 15.39 5 25636 172 90602634
Ear pain 18.00 15.39 46 25595 57656 90545150
Myocardial infarction 17.94 15.39 4 25637 105968 90496838
Simple partial seizures 17.82 15.39 7 25634 728 90602078
Thinking abnormal 17.47 15.39 19 25622 11713 90591093
Subcutaneous drug absorption impaired 16.88 15.39 20 25621 13525 90589281
Dislocation of vertebra 16.82 15.39 44 25597 55924 90546882
Anaemia 16.73 15.39 48 25593 352754 90250052
Cerebrovascular accident 16.71 15.39 7 25634 123526 90479280
Platelet count decreased 16.63 15.39 9 25632 136960 90465846
Photophobia 16.63 15.39 25 25616 21244 90581562
Blood pressure increased 16.36 15.39 19 25622 197198 90405608
Acne fulminans 16.31 15.39 3 25638 14 90602792
Treatment failure 16.30 15.39 144 25497 303784 90299022
Gambling 16.06 15.39 5 25636 261 90602545
Irritable bowel syndrome 15.99 15.39 107 25534 207341 90395465
Wound 15.97 15.39 143 25498 302837 90299969
Vomiting 15.92 15.39 312 25329 787981 89814825
Atrial fibrillation 15.90 15.39 9 25632 133602 90469204
Papule 15.63 15.39 15 25626 7987 90594819
Chromosomal deletion 15.57 15.39 4 25637 103 90602703

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Differentiation syndrome 1171.85 23.70 191 3484 1622 42616038
Idiopathic intracranial hypertension 207.01 23.70 39 3636 791 42616869
Hyperleukocytosis 137.01 23.70 34 3641 2574 42615086
Electrocardiogram QT prolonged 115.96 23.70 64 3611 47881 42569779
Acute myeloid leukaemia 92.85 23.70 43 3632 22213 42595447
Haematopoietic neoplasm 81.63 23.70 12 3663 45 42617615
Leukaemia recurrent 76.56 23.70 20 3655 1856 42615804
Product use in unapproved indication 64.08 23.70 79 3596 184377 42433283
Scrotal ulcer 55.59 23.70 12 3663 489 42617171
Cytogenetic abnormality 48.19 23.70 12 3663 919 42616741
Off label use 41.14 23.70 134 3541 638201 41979459
Acute promyelocytic leukaemia 40.68 23.70 10 3665 726 42616934
Large granular lymphocytosis 38.96 23.70 8 3667 255 42617405
Hypokalaemia 37.32 23.70 38 3637 71683 42545977
Febrile neutropenia 36.88 23.70 61 3614 185642 42432018
Myelodysplastic syndrome 35.65 23.70 23 3652 22722 42594938
Hypomagnesaemia 35.53 23.70 25 3650 28463 42589197
IIIrd nerve paralysis 32.78 23.70 8 3667 563 42617097
Neutropenia 28.72 23.70 57 3618 199374 42418286
Hypercalcaemia 27.65 23.70 18 3657 18040 42599620
White blood cell count increased 27.36 23.70 26 3649 45061 42572599
Bone marrow necrosis 26.69 23.70 6 3669 295 42617365
Jugular vein thrombosis 26.46 23.70 9 3666 2065 42615595
Extremity necrosis 25.47 23.70 9 3666 2310 42615350
Lymphopenia 24.76 23.70 18 3657 21545 42596115
Diffusion-weighted brain MRI abnormal 24.44 23.70 4 3671 34 42617626

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Differentiation syndrome 1847.97 17.06 356 26363 2688 110559892
Taste disorder 342.06 17.06 207 26512 65180 110497400
Blepharospasm 313.86 17.06 184 26535 54667 110507913
Epilepsy 228.24 17.06 191 26528 100018 110462562
Idiopathic intracranial hypertension 227.39 17.06 69 26650 3883 110558697
Overlap syndrome 171.38 17.06 69 26650 8990 110553590
Product quality issue 158.95 17.06 139 26580 77160 110485420
Onychomadesis 158.80 17.06 112 26607 45551 110517029
Infusion site reaction 158.77 17.06 80 26639 17602 110544978
Back injury 145.98 17.06 108 26611 47291 110515289
Myelodysplastic syndrome transformation 141.28 17.06 34 26685 783 110561797
Gastrooesophageal reflux disease 137.04 17.06 192 26527 179784 110382796
Maternal exposure during pregnancy 136.52 17.06 231 26488 254652 110307928
Product use in unapproved indication 127.61 17.06 312 26407 447065 110115515
Memory impairment 115.51 17.06 186 26533 196758 110365822
Breast cancer stage III 112.45 17.06 116 26603 79001 110483579
Hyperleukocytosis 111.96 17.06 39 26680 3400 110559180
Live birth 104.43 17.06 105 26614 69379 110493201
Paraesthesia 101.17 17.06 213 26506 276308 110286272
Neck pain 100.66 17.06 136 26583 122994 110439586
Peripheral venous disease 99.64 17.06 112 26607 84005 110478575
Leukaemia recurrent 88.61 17.06 32 26687 3099 110559481
Nail disorder 87.89 17.06 88 26631 57847 110504733
Hypoaesthesia 84.05 17.06 214 26505 314009 110248571
Intracranial pressure increased 83.98 17.06 44 26675 10491 110552089
Migraine 83.25 17.06 149 26570 171503 110391077
Acute myeloid leukaemia 81.27 17.06 70 26649 38040 110524540
Rheumatic fever 76.27 17.06 119 26600 122460 110440120
Abdominal pain upper 75.60 17.06 220 26499 348891 110213689
Night sweats 69.74 17.06 120 26599 133863 110428717
Lip dry 69.12 17.06 102 26617 99981 110462599
Wound infection 69.06 17.06 100 26619 96365 110466215
Osteoarthritis 68.28 17.06 142 26577 182481 110380099
Facet joint syndrome 65.88 17.06 98 26621 96730 110465850
Bursitis 65.85 17.06 115 26604 129803 110432777
Haematopoietic neoplasm 63.01 17.06 12 26707 84 110562496
Drug intolerance 62.55 17.06 228 26491 406284 110156296
Hypercholesterolaemia 61.89 17.06 92 26627 90745 110471835
Liver function test increased 59.35 17.06 89 26630 88459 110474121
Pericarditis 57.26 17.06 148 26571 218966 110343614
Psoriatic arthropathy 56.76 17.06 138 26581 196623 110365957
Toxicity to various agents 54.43 17.06 24 26695 480531 110082049
Bone marrow necrosis 49.86 17.06 13 26706 418 110562162
Cytogenetic abnormality 48.44 17.06 16 26703 1186 110561394
Joint range of motion decreased 48.20 17.06 97 26622 121735 110440845
Obesity 46.95 17.06 92 26627 113259 110449321
Completed suicide 46.70 17.06 3 26716 242378 110320202
Folliculitis 46.66 17.06 116 26603 167537 110395043
Second primary malignancy 46.46 17.06 37 26682 18031 110544549
Blood cholesterol increased 45.40 17.06 122 26597 184663 110377917
Wound 45.29 17.06 142 26577 234295 110328285
Gait inability 45.17 17.06 101 26618 136275 110426305
Injury 44.53 17.06 118 26601 177147 110385433
Normal newborn 44.22 17.06 39 26680 21857 110540723
Muscle injury 44.11 17.06 102 26617 140705 110421875
Sleep disorder 43.73 17.06 126 26593 198518 110364062
Electrocardiogram QT prolonged 43.39 17.06 87 26632 108873 110453707
Death 42.97 17.06 64 26655 698805 109863775
Abortion spontaneous 42.90 17.06 47 26672 34235 110528345
Myelodysplastic syndrome 42.82 17.06 49 26670 37435 110525145
Type 2 diabetes mellitus 42.52 17.06 116 26603 177116 110385464
Blister 42.34 17.06 136 26583 227240 110335340
Hypotension 41.80 17.06 39 26680 523810 110038770
Hyponatraemia 41.04 17.06 3 26716 217650 110344930
Inflammation 41.02 17.06 121 26598 193117 110369463
Fatigue 38.76 17.06 157 26562 1215801 109346779
Fall 38.33 17.06 54 26665 603428 109959152
Therapeutic product effect incomplete 38.22 17.06 130 26589 223675 110338905
Anti-cyclic citrullinated peptide antibody positive 37.72 17.06 113 26606 181871 110380709
Cough 37.26 17.06 34 26685 461607 110100973
Dyspnoea 37.13 17.06 140 26579 1106732 109455848
Depression 36.75 17.06 163 26556 317172 110245408
Musculoskeletal pain 36.39 17.06 112 26607 182911 110379669
Fibromyalgia 36.25 17.06 107 26612 170802 110391778
Irritable bowel syndrome 35.97 17.06 104 26615 164111 110398469
Treatment failure 35.65 17.06 147 26572 277087 110285493
Dysphoria 35.25 17.06 21 26698 6407 110556173
Breast cancer stage II 35.07 17.06 38 26681 27337 110535243
Rheumatoid arthritis 34.77 17.06 154 26565 299459 110263121
Dry mouth 34.01 17.06 116 26603 199832 110362748
Intentional product use issue 33.90 17.06 134 26585 247772 110314808
Dehydration 33.17 17.06 13 26706 279498 110283082
Urinary tract infection 32.86 17.06 19 26700 326263 110236317
Duodenal ulcer perforation 32.81 17.06 106 26613 177594 110384986
Malaise 31.13 17.06 73 26646 671746 109890834
Synovitis 31.13 17.06 140 26579 273952 110288628
Acute promyelocytic leukaemia 30.95 17.06 13 26706 1883 110560697
Contraindicated product administered 29.86 17.06 129 26590 248138 110314442
Product use issue 29.47 17.06 151 26568 311544 110251036
Subcutaneous drug absorption impaired 29.46 17.06 20 26699 7639 110554941
Dislocation of vertebra 29.36 17.06 44 26675 43677 110518903
Dermatitis atopic 28.51 17.06 33 26686 25508 110537072
Disseminated intravascular coagulation 28.37 17.06 42 26677 41244 110521336
Therapeutic product effect decreased 27.90 17.06 125 26594 244191 110318389
Papilloedema 27.68 17.06 19 26700 7390 110555190
Haemorrhagic diathesis 27.45 17.06 19 26700 7489 110555091
Urticaria 27.09 17.06 150 26569 318707 110243873
Pemphigus 26.96 17.06 113 26606 214457 110348123
Scrotal ulcer 26.50 17.06 8 26711 442 110562138
Liver injury 26.22 17.06 88 26631 150325 110412255
Lung disorder 25.97 17.06 99 26620 179948 110382632
Large granular lymphocytosis 25.30 17.06 8 26711 516 110562064
Atrial fibrillation 25.14 17.06 12 26707 229630 110332950
Appetite disorder 25.11 17.06 20 26699 9749 110552831
Blood pressure increased 24.68 17.06 16 26703 258357 110304223
Product administration interrupted 24.59 17.06 21 26698 11271 110551309
C-reactive protein increased 24.50 17.06 111 26608 217808 110344772
Lupus vulgaris 24.05 17.06 35 26684 33848 110528732
Skin warm 24.05 17.06 19 26700 9151 110553429
Somnolence 23.87 17.06 22 26697 297427 110265153
Polyarteritis nodosa 23.79 17.06 8 26711 627 110561953
Chromosomal deletion 23.57 17.06 6 26713 175 110562405
Stomatitis 23.53 17.06 128 26591 270114 110292466
Acute kidney injury 23.50 17.06 77 26642 635353 109927227
Glossodynia 23.43 17.06 111 26608 221893 110340687
Hypercalcaemia 23.23 17.06 41 26678 46616 110515964
Product label confusion 23.17 17.06 28 26691 22649 110539931
Helicobacter infection 23.01 17.06 96 26623 181781 110380799
Hypocholesterolaemia 22.89 17.06 16 26703 6405 110556175
Muscular weakness 22.52 17.06 119 26600 248349 110314231
Bradycardia 22.51 17.06 5 26714 155512 110407068
Photophobia 21.85 17.06 29 26690 25742 110536838
Ear pain 21.78 17.06 43 26676 53183 110509397
Rash vesicular 21.74 17.06 22 26697 14630 110547950
Overdose 21.63 17.06 15 26704 233779 110328801
Chloroma 21.52 17.06 8 26711 840 110561740
Weight increased 21.46 17.06 174 26545 419470 110143110
Lower respiratory tract infection fungal 21.44 17.06 8 26711 849 110561731
Impaired healing 21.22 17.06 99 26620 196618 110365962
Off label use 21.12 17.06 492 26227 1499693 109062887
Constipation 20.77 17.06 34 26685 357752 110204828
Diffusion-weighted brain MRI abnormal 20.01 17.06 4 26715 37 110562543
Ciliary body melanoma 19.91 17.06 3 26716 3 110562577
Myocardial infarction 19.60 17.06 11 26708 192072 110370508
Arthropathy 19.15 17.06 127 26592 287395 110275185
Gastrointestinal haemorrhage 19.14 17.06 8 26711 165510 110397070
Systemic lupus erythematosus 18.58 17.06 115 26604 254223 110308357
Platelet count decreased 18.54 17.06 17 26702 230426 110332154
Anaemia 18.40 17.06 69 26650 547017 110015563
Haemoglobin decreased 18.12 17.06 20 26699 248707 110313873
Arthritis infective 17.98 17.06 17 26702 10412 110552168
Blood glucose increased 17.74 17.06 5 26714 132491 110430089
IIIrd nerve paralysis 17.66 17.06 8 26711 1389 110561191
Pustular psoriasis 17.63 17.06 19 26700 13586 110548994
Renal impairment 17.55 17.06 12 26707 188433 110374147
Syncope 17.44 17.06 14 26705 202522 110360058
Muscle spasms 17.41 17.06 121 26598 278036 110284544
Oesophageal mass 17.40 17.06 4 26715 75 110562505
Exposure during pregnancy 17.14 17.06 83 26636 167341 110395239

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC D10AD01 DERMATOLOGICALS
ANTI-ACNE PREPARATIONS
ANTI-ACNE PREPARATIONS FOR TOPICAL USE
Retinoids for topical use in acne
ATC D10AD51 DERMATOLOGICALS
ANTI-ACNE PREPARATIONS
ANTI-ACNE PREPARATIONS FOR TOPICAL USE
Retinoids for topical use in acne
ATC L01XF01 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
OTHER ANTINEOPLASTIC AGENTS
Retinoids for cancer treatment
FDA CS M0018962 Retinoids
MeSH PA D000970 Antineoplastic Agents
MeSH PA D003879 Dermatologic Agents
MeSH PA D007641 Keratolytic Agents
FDA EPC N0000175607 Retinoid
CHEBI has role CHEBI:77746 human metabolite

Related Drugs by ATC class:

D10AD Retinoids for topical use in acne 5 drugs
adapaleneisotretinoinmotretinideretinoltrifarotene
L01XF Retinoids for cancer treatment 2 drugs
alitretinoinbexarotene

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Chloasma indication 36209000
Acne vulgaris indication 88616000
Acute promyelocytic leukemia, FAB M3 indication 110004001
Hyperkeratosis indication 396228006
Facial Fine Wrinkling indication
Solar Lentigines indication
Fine Wrinkling indication
Severe Recalcitrant Nodular Acne indication
Kaposi's Sarcoma Skin Lesions indication
Mottle Hyperpigmentation indication
Keratosis follicularis off-label use 48611009 DOID:2734
Lamellar ichthyosis off-label use 205550003
Plane wart off-label use 240539000
Primary cutaneous T-cell lymphoma off-label use 400122007
Severe Recalcitrant Nodular Rosacea off-label use
Osteomalacia contraindication 4598005 DOID:10573
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Rectal hemorrhage contraindication 12063002
Hypercholesterolemia contraindication 13644009
Hearing loss contraindication 15188001
Agranulocytosis contraindication 17182001 DOID:12987
Myocardial infarction contraindication 22298006 DOID:5844
Sunburn contraindication 23346002
Atopic dermatitis contraindication 24079001 DOID:3310
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Crohn's disease contraindication 34000006
Depressive disorder contraindication 35489007
Eczema contraindication 43116000
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Vitiligo contraindication 56727007 DOID:12306
Anorexia nervosa contraindication 56882008 DOID:8689
Tinnitus contraindication 60862001
Corneal opacity contraindication 64634000
Ulcerative colitis contraindication 64766004 DOID:8577
Osteoporosis contraindication 64859006 DOID:11476
Benign intracranial hypertension contraindication 68267002 DOID:11459
Psychotic disorder contraindication 69322001
Diabetes mellitus contraindication 73211009 DOID:9351
Disorder of bone contraindication 76069003 DOID:0080001
Congenital neutropenia contraindication 89655007
Kidney disease contraindication 90708001 DOID:557
Venous thrombosis contraindication 111293003
Leukocytosis contraindication 111583006
Mycosis fungoides contraindication 118618005
Inflammatory disease of liver contraindication 128241005
Bleeding contraindication 131148009
Liver function tests abnormal contraindication 166603001
Acute pancreatitis contraindication 197456007 DOID:2913
Disease of liver contraindication 235856003 DOID:409
Telangiectasia disorder contraindication 247479008
Dyspnea contraindication 267036007
Edema contraindication 267038008
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Keratoconjunctivitis sicca contraindication 302896008 DOID:12895
Neutropenic disorder contraindication 303011007 DOID:1227
Pericardial effusion contraindication 373945007 DOID:118
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Fever contraindication 386661006
Pseudomembranous enterocolitis contraindication 397683000
Atrophoderma contraindication 399979006
Peripheral vascular disease contraindication 400047006
Severe diarrhea contraindication 409587002
Breastfeeding (mother) contraindication 413712001
Obesity contraindication 414916001 DOID:9970
Denuded skin contraindication 418242004
Retinoic acid syndrome contraindication 450887006
Pulmonary Infiltrates contraindication
Pleural Effusions contraindication
Predisposition To Hypertriglyceridemia contraindication




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.17 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
3%;0.1% TWYNEO MAYNE PHARMA N214902 July 26, 2021 RX CREAM TOPICAL 9868103 Aug. 8, 2028 TOPICAL TREATMENT OF ACNE VULGARIS IN ADULTS AND PEDIATRIC PATIENTS 9 YEARS OF AGE AND OLDER
3%;0.1% TWYNEO MAYNE PHARMA N214902 July 26, 2021 RX CREAM TOPICAL 10653899 Dec. 30, 2030 TOPICAL TREATMENT OF ACNE VULGARIS IN ADULTS AND PEDIATRIC PATIENTS 9 YEARS OF AGE AND OLDER
3%;0.1% TWYNEO MAYNE PHARMA N214902 July 26, 2021 RX CREAM TOPICAL 12070629 Dec. 30, 2030 TOPICAL TREATMENT OF ACNE
3%;0.1% TWYNEO MAYNE PHARMA N214902 July 26, 2021 RX CREAM TOPICAL 10420743 July 12, 2038 TOPICAL TREATMENT OF ACNE VULGARIS IN ADULTS AND PEDIATRIC PATIENTS 9 YEARS OF AGE AND OLDER
3%;0.1% TWYNEO MAYNE PHARMA N214902 July 26, 2021 RX CREAM TOPICAL 12357602 July 12, 2038 TOPICAL TREATMENT OF ACNE
0.05% ALTRENO DOW PHARM N209353 Aug. 23, 2018 RX LOTION TOPICAL 10653656 Aug. 22, 2038 TOPICAL TREATMENT OF ACNE VULGARIS IN PATIENTS 9 YEARS OF AGE AND OLDER
0.05% ALTRENO DOW PHARM N209353 Aug. 23, 2018 RX LOTION TOPICAL 11324710 Aug. 22, 2038 TOPICAL TREATMENT OF ACNE VULGARIS IN PATIENTS 9 YEARS OF AGE AND OLDER
3%;0.1% TWYNEO MAYNE PHARMA N214902 July 26, 2021 RX CREAM TOPICAL 12295935 Dec. 27, 2040 TOPICAL TREATMENT OF ACNE
3%;0.1% TWYNEO MAYNE PHARMA N214902 July 26, 2021 RX CREAM TOPICAL 12133919 May 23, 2041 TOPICAL TREATMENT OF ACNE
3%;0.1% TWYNEO MAYNE PHARMA N214902 July 26, 2021 RX CREAM TOPICAL 12257348 May 23, 2041 TOPICAL TREATMENT OF ACNE
3%;0.1% TWYNEO MAYNE PHARMA N214902 July 26, 2021 RX CREAM TOPICAL 12491163 May 23, 2041 TOPICAL TREATMENT OF ACNE

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Retinoic acid receptor beta Nuclear hormone receptor AGONIST EC50 6.70 WOMBAT-PK CHEMBL
Retinoic acid receptor gamma Nuclear hormone receptor AGONIST EC50 6.70 WOMBAT-PK CHEMBL
Retinoic acid receptor alpha Nuclear hormone receptor AGONIST EC50 6.70 WOMBAT-PK CHEMBL
Nuclear receptor ROR-alpha Nuclear hormone receptor IC50 6.70 CHEMBL
Retinoic acid receptor RXR-alpha Nuclear hormone receptor Ki 9.40 CHEMBL
Retinoic acid receptor RXR-beta Nuclear hormone receptor Ki 9.30 CHEMBL
Retinoic acid receptor RXR-gamma Nuclear hormone receptor Ki 8.85 CHEMBL
Peroxisome proliferator-activated receptor delta Nuclear hormone receptor AGONIST Kd 7.80 IUPHAR
Nuclear receptor ROR-beta Nuclear hormone receptor ANTAGONIST IC50 9.82 IUPHAR
Nuclear receptor ROR-gamma Nuclear hormone receptor IC50 6.70 CHEMBL
Mitogen-activated protein kinase 1 Kinase IC50 6.24 DRUG MATRIX
Nuclear receptor subfamily 2 group E member 1 Nuclear hormone receptor AGONIST EC50 5.74 IUPHAR
Amyloid beta A4 protein Membrane other IC50 6.75 CHEMBL
Nuclear receptor subfamily 2 group C member 2 Nuclear other AGONIST EC50 4.62 IUPHAR
Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Enzyme IC50 6.09 CHEMBL
5-hydroxytryptamine receptor 2B GPCR Ki 6.64 DRUG MATRIX
Alpha-synuclein Transporter IC50 5.52 CHEMBL
Adenosine receptor A3 GPCR Ki 5.53 DRUG MATRIX
11-cis retinol dehydrogenase Enzyme Ki 7 WOMBAT-PK
Cellular retinoic acid-binding protein 1 Cytosolic other IC50 6.43 CHEMBL
Retinoic acid receptor RXR-beta Transcription factor Kd 6.51 CHEMBL
Retinoic acid receptor RXR-gamma Transcription factor Kd 6.46 CHEMBL
Cellular retinoic acid-binding protein 1 Cytosolic other Kd 9.40 CHEMBL
Cellular retinoic acid-binding protein 2 Cytosolic other Kd 8.70 CHEMBL
Retinoic acid receptor alpha Transcription factor Kd 7.82 CHEMBL
Retinoic acid receptor RXR-alpha Transcription factor Kd 6 CHEMBL
Retinoic acid receptor beta Transcription factor Kd 7.89 CHEMBL
Retinoic acid receptor gamma Transcription factor Kd 7.74 CHEMBL
Indoleamine 2,3-dioxygenase 2 Enzyme IC50 4.54 CHEMBL

External reference:

IDSource
4018550 VUID
N0000146871 NUI
D00094 KEGG_DRUG
4018550 VANDF
C0040845 UMLSCUI
CHEBI:15367 CHEBI
3KV PDB_CHEM_ID
CHEMBL38 ChEMBL_ID
DB00755 DRUGBANK_ID
D014212 MESH_DESCRIPTOR_UI
444795 PUBCHEM_CID
2644 IUPHAR_LIGAND_ID
2875 INN_ID
5688UTC01R UNII
10753 RXNORM
46802 MMSL
5610 MMSL
d03863 MMSL
001954 NDDF
387305002 SNOMEDCT_US
54972005 SNOMEDCT_US
5688UTC01R INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Altreno HUMAN PRESCRIPTION DRUG LABEL 1 0187-0005 LOTION 0.50 mg TOPICAL NDA 24 sections
Retin-A MICRO HUMAN PRESCRIPTION DRUG LABEL 1 0187-5140 GEL 1 mg TOPICAL NDA 24 sections
Retin-A MICRO HUMAN PRESCRIPTION DRUG LABEL 1 0187-5144 GEL 0.40 mg TOPICAL NDA 24 sections
Retin-A MICRO HUMAN PRESCRIPTION DRUG LABEL 1 0187-5146 GEL 0.60 mg TOPICAL NDA 24 sections
Retin-A MICRO HUMAN PRESCRIPTION DRUG LABEL 1 0187-5148 GEL 0.80 mg TOPICAL NDA 24 sections
Renova HUMAN PRESCRIPTION DRUG LABEL 1 0187-5150 CREAM 0.20 mg TOPICAL NDA 25 sections
Retin-A HUMAN PRESCRIPTION DRUG LABEL 1 0187-5160 CREAM 0.25 mg TOPICAL NDA 21 sections
Retin-A HUMAN PRESCRIPTION DRUG LABEL 1 0187-5162 CREAM 0.50 mg TOPICAL NDA 21 sections
Retin-A HUMAN PRESCRIPTION DRUG LABEL 1 0187-5164 CREAM 1 mg TOPICAL NDA 21 sections
Retin-A HUMAN PRESCRIPTION DRUG LABEL 1 0187-5170 GEL 0.25 mg TOPICAL NDA 21 sections
Retin-A HUMAN PRESCRIPTION DRUG LABEL 1 0187-5172 GEL 0.10 mg TOPICAL NDA 21 sections
TWYNEO HUMAN PRESCRIPTION DRUG LABEL 2 0299-5945 CREAM 1 mg TOPICAL NDA 26 sections
TRI-LUMA HUMAN PRESCRIPTION DRUG LABEL 3 0299-5950 CREAM 0.50 mg TOPICAL NDA 24 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8082 CREAM 0.25 mg TOPICAL NDA authorized generic 20 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8083 CREAM 0.50 mg TOPICAL NDA authorized generic 20 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8084 CREAM 1 mg TOPICAL NDA authorized generic 20 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8085 GEL 0.10 mg TOPICAL NDA authorized generic 20 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8086 GEL 0.25 mg TOPICAL NDA authorized generic 20 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8090 GEL 0.50 mg TOPICAL ANDA 22 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0472-0117 CREAM 0.25 mg TOPICAL NDA authorized generic 22 sections
Clindamycin Phosphate and Tretinoin HUMAN PRESCRIPTION DRUG LABEL 2 0472-1790 GEL 0.25 mg TOPICAL ANDA 17 sections
TRETINOIN HUMAN PRESCRIPTION DRUG LABEL 1 0574-2201 CREAM 1 mg TOPICAL ANDA 21 sections
TRETINOIN HUMAN PRESCRIPTION DRUG LABEL 1 0574-2205 CREAM 0.50 mg TOPICAL ANDA 21 sections
TRETINOIN HUMAN PRESCRIPTION DRUG LABEL 1 0574-2225 CREAM 0.25 mg TOPICAL ANDA 21 sections
TRETINOIN HUMAN PRESCRIPTION DRUG LABEL 1 0574-2301 GEL 0.10 mg TOPICAL ANDA 21 sections
TRETINOIN HUMAN PRESCRIPTION DRUG LABEL 1 0574-2325 GEL 0.25 mg TOPICAL ANDA 21 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0904-6867 CAPSULE 10 mg ORAL ANDA 27 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 10370-268 CAPSULE 10 mg ORAL ANDA 28 sections
Atralin HUMAN PRESCRIPTION DRUG LABEL 1 13548-070 GEL 0.05 g TOPICAL NDA 25 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 14290-281 CREAM 1 mg TOPICAL NDA 20 sections