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naratriptan 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| serotonin (5-HT1) receptor agonists, sumatriptan derivatives | 1884 | 121679-13-8 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 2.50 | mg | O |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| BDDCS (Biopharmaceutical Drug Disposition Classification System) | 3 | Benet LZ, Broccatelli F, Oprea TI |
| S (Water solubility) | 35 mg/mL | Benet LZ, Broccatelli F, Oprea TI |
| EoM (Fraction excreted unchanged in urine) | 50 % | Benet LZ, Broccatelli F, Oprea TI |
| MRTD (Maximum Recommended Therapeutic Daily Dose) | 0.21 µM/kg/day | Contrera JF, Matthews EJ, Kruhlak NL, Benz RD |
| BA (Bioavailability) | 69 % | Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H |
| Vd (Volume of distribution) | 2.40 L/kg | Lombardo F, Berellini G, Obach RS |
| CL (Clearance) | 6.60 mL/min/kg | Lombardo F, Berellini G, Obach RS |
| fu (Fraction unbound in plasma) | 0.70 % | Lombardo F, Berellini G, Obach RS |
| t_half (Half-life) | 6.60 hours | Lombardo F, Berellini G, Obach RS |
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| azlogd74 | LogD at pH 7.4 | -0.235 | High | 1 | |
| caco2-efflux | Caco-2 efflux ratio (BA/AB) | 3.597 | High | 1 | |
| caco2-intrinsic-papp | Caco-2 intrinsic apparent permeability | 0.445 | 10^-6 cm/s | High | 1 |
| dh-clint | Dog hepatocyte intrinsic clearance | 1.832 | uL/min/10^6 cells | High | 1 |
| dppb | Dog plasma protein binding (% unbound) | 70.860 | % | High | 1 |
| fcs-ppb | Fetal calf serum protein binding (% unbound) | 67.380 | % | High | 1 |
| herg | hERG pIC50 | 4.484 | pIC50 | High | 1 |
| hh-clint | Human hepatocyte intrinsic clearance | 1.107 | uL/min/10^6 cells | High | 1 |
| hlm-clint | Human liver microsomal intrinsic clearance | 3.170 | uL/min/mg protein | High | 1 |
| hppb | Human plasma protein binding (% unbound) | 75.850 | % | High | 1 |
| kinase-safety-class | ACVR2B,AXL,BRAF,CAMK2D,CDK5,CDK9,EIF2AK3,ERBB2,GRK2,ITK,NTRK2,PDK1,PDK2,PDK4,PRKDC | 15 | |||
| kinase-selectivity-class | AKT3,AXL,CAMK2D,CDK4,CLK4,PDK1,PRKACA,PRKCD,SIK2,TEK | 10 | |||
| mdck-mdr1-efflux | MDCK-MDR1 efflux ratio | 1.374 | High | 1 | |
| mh-clint | Mouse hepatocyte intrinsic clearance | 6.745 | High | 1 | |
| mppb | Mouse plasma protein binding (% unbound) | 75.080 | High | 1 | |
| nih-mdck-mdr1-efflux | NIH MDCK-MDR1 efflux ratio | 2.239 | High | 1 | |
| pfas-class | PFAS structural alert (1 = True, 0 = False) | 0 | |||
| pppb | Pig plasma protein binding (% unbound) | 85.280 | % | High | 1 |
| rh-clint | Rat hepatocyte intrinsic clearance | 1.538 | uL/min/10^6 cells | High | 1 |
| rh-fuinc | Rat hepatocyte fraction unbound in incubation | 83.560 | % | High | 1 |
| rppb | Rat plasma protein binding (% unbound) | 71.200 | % | High | 1 |
| solubility-dd | Solubility at pH 7.4 in DMSO | 905.733 | uM | High | 1 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| Feb. 10, 1998 | FDA | GLAXOSMITHKLINE LLC |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Neovascularisation | 282.49 | 23.09 | 50 | 3578 | 1580 | 90623239 |
| Paradoxical drug reaction | 219.48 | 23.09 | 50 | 3578 | 5716 | 90619103 |
| Anuria | 172.65 | 23.09 | 50 | 3578 | 14768 | 90610051 |
| Extrapyramidal disorder | 167.93 | 23.09 | 50 | 3578 | 16253 | 90608566 |
| Migraine | 140.76 | 23.09 | 90 | 3538 | 190302 | 90434517 |
| Drug ineffective for unapproved indication | 93.67 | 23.09 | 48 | 3580 | 66596 | 90558223 |
| Dyspepsia | 55.88 | 23.09 | 53 | 3575 | 198107 | 90426712 |
| Cerebral vasoconstriction | 53.98 | 23.09 | 12 | 3616 | 1222 | 90623597 |
| Cough | 50.99 | 23.09 | 68 | 3560 | 368894 | 90255925 |
| Weight decreased | 50.96 | 23.09 | 69 | 3559 | 379841 | 90244978 |
| Abdominal pain | 50.26 | 23.09 | 70 | 3558 | 395651 | 90229168 |
| Treatment failure | 43.47 | 23.09 | 57 | 3571 | 303871 | 90320948 |
| Nausea | 37.55 | 23.09 | 113 | 3515 | 1110203 | 89514616 |
| Drug ineffective | 31.13 | 23.09 | 123 | 3505 | 1384175 | 89240644 |
| Burns third degree | 30.99 | 23.09 | 6 | 3622 | 310 | 90624509 |
| Opisthotonus | 29.78 | 23.09 | 6 | 3622 | 381 | 90624438 |
| Herpes simplex reactivation | 29.06 | 23.09 | 7 | 3621 | 1012 | 90623807 |
| Chloasma | 28.25 | 23.09 | 5 | 3623 | 157 | 90624662 |
| Reversible cerebral vasoconstriction syndrome | 27.15 | 23.09 | 9 | 3619 | 4121 | 90620698 |
| Bronchial obstruction | 25.55 | 23.09 | 7 | 3621 | 1682 | 90623137 |
| Dust allergy | 25.22 | 23.09 | 6 | 3622 | 823 | 90623996 |
| Diarrhoea | 24.79 | 23.09 | 88 | 3540 | 939102 | 89685717 |
| Consciousness fluctuating | 24.44 | 23.09 | 6 | 3622 | 940 | 90623879 |
| Spinal cord infarction | 24.21 | 23.09 | 5 | 3623 | 359 | 90624460 |
FDA Adverse Event Reporting System (Male)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Medication overuse headache | 63.95 | 49.05 | 8 | 185 | 216 | 42620926 |
FDA Adverse Event Reporting System (Geriatric)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Neovascularisation | 292.34 | 26.15 | 50 | 3362 | 1687 | 110584200 |
| Paradoxical drug reaction | 205.99 | 26.15 | 50 | 3362 | 9767 | 110576120 |
| Anuria | 161.03 | 26.15 | 50 | 3362 | 24291 | 110561596 |
| Extrapyramidal disorder | 152.64 | 26.15 | 50 | 3362 | 28817 | 110557070 |
| Migraine | 143.33 | 26.15 | 80 | 3332 | 171572 | 110414315 |
| Drug ineffective for unapproved indication | 94.15 | 26.15 | 51 | 3361 | 102787 | 110483100 |
| Dyspepsia | 69.65 | 26.15 | 53 | 3359 | 190912 | 110394975 |
| Treatment failure | 58.11 | 26.15 | 56 | 3356 | 277178 | 110308709 |
| Cough | 56.16 | 26.15 | 70 | 3342 | 461571 | 110124316 |
| Cerebral vasoconstriction | 54.76 | 26.15 | 12 | 3400 | 1489 | 110584398 |
| Abdominal pain | 51.85 | 26.15 | 71 | 3341 | 512918 | 110072969 |
| Weight decreased | 50.67 | 26.15 | 67 | 3345 | 467990 | 110117897 |
| Nausea | 44.38 | 26.15 | 109 | 3303 | 1235581 | 109350306 |
| Burns third degree | 42.15 | 26.15 | 8 | 3404 | 485 | 110585402 |
| Drug ineffective | 36.64 | 26.15 | 116 | 3296 | 1520424 | 109065463 |
| Bronchial obstruction | 32.07 | 26.15 | 9 | 3403 | 3070 | 110582817 |
| Herpes simplex reactivation | 28.34 | 26.15 | 7 | 3405 | 1461 | 110584426 |
| Reversible cerebral vasoconstriction syndrome | 28.20 | 26.15 | 9 | 3403 | 4752 | 110581135 |
| Nasal discharge discolouration | 27.26 | 26.15 | 8 | 3404 | 3193 | 110582694 |
| Opisthotonus | 27.10 | 26.15 | 6 | 3406 | 780 | 110585107 |
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| ATC | N02CC02 | NERVOUS SYSTEM ANALGESICS ANTIMIGRAINE PREPARATIONS Selective serotonin (5HT1) agonists |
| MeSH PA | D002317 | Cardiovascular Agents |
| MeSH PA | D014662 | Vasoconstrictor Agents |
| MeSH PA | D017366 | Serotonin Receptor Agonists |
| MeSH PA | D018377 | Neurotransmitter Agents |
| MeSH PA | D018490 | Serotonin Agents |
| MeSH PA | D058825 | Serotonin 5-HT1 Receptor Agonists |
| FDA MoA | N0000175763 | Serotonin 1b Receptor Agonists |
| FDA MoA | N0000175764 | Serotonin 1d Receptor Agonists |
| FDA EPC | N0000175765 | Serotonin-1b and Serotonin-1d Receptor Agonist |
| CHEBI has role | CHEBI:35941 | serotonergic agonist |
| CHEBI has role | CHEBI:50514 | vasoconstrictor agent |
Related Drugs by ATC class:
N02CC Selective serotonin (5HT1) agonists 8 drugs
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| Migraine | indication | 37796009 | DOID:6364 |
| Hypercholesterolemia | contraindication | 13644009 | |
| Myocardial infarction | contraindication | 22298006 | DOID:5844 |
| Hypertensive disorder | contraindication | 38341003 | DOID:10763 |
| Acute nephropathy | contraindication | 58574008 | |
| Hemiplegic migraine | contraindication | 59292006 | |
| Hepatic failure | contraindication | 59927004 | |
| Cerebrovascular disease | contraindication | 62914000 | DOID:6713 |
| Diabetes mellitus | contraindication | 73211009 | DOID:9351 |
| Prinzmetal angina | contraindication | 87343002 | |
| Angina pectoris | contraindication | 194828000 | |
| Cerebrovascular accident | contraindication | 230690007 | |
| Transient ischemic attack | contraindication | 266257000 | DOID:224 |
| Cardiovascular event risk | contraindication | 395112001 | |
| Peripheral vascular disease | contraindication | 400047006 | |
| Disorder of coronary artery | contraindication | 414024009 | |
| Myocardial ischemia | contraindication | 414795007 | DOID:3393 |
| Obesity | contraindication | 414916001 | DOID:9970 |
| Hypertensive urgency | contraindication | 443482000 |
🐶 Veterinary Drug Use
None
🐶 Veterinary products
None
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 11.21 | acidic |
| pKa2 | 13.86 | acidic |
| pKa3 | 9.38 | Basic |
Orange Book patent data (new drug applications)
None
Orange Book exclusivity data (new drug applications)
None
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA source |
|---|---|---|---|---|---|---|---|---|---|
| 5-hydroxytryptamine receptor 1B | GPCR | AGONIST | Ki | 8.48 | CHEMBL | CHEMBL | |||
| 5-hydroxytryptamine receptor 1D | GPCR | AGONIST | EC50 | 8.80 | WOMBAT-PK | CHEMBL | |||
| 5-hydroxytryptamine receptor 1A | GPCR | Ki | 7.35 | CHEMBL | |||||
| 5-hydroxytryptamine receptor 1F | GPCR | AGONIST | Ki | 8.20 | IUPHAR | ||||
| 5-hydroxytryptamine receptor 1E | GPCR | AGONIST | Ki | 7.70 | IUPHAR |
External reference:
| ID | Source |
|---|---|
| 4024101 | VUID |
| N0000022106 | NUI |
| D00674 | KEGG_DRUG |
| 143388-64-1 | SECONDARY_CAS_RN |
| 4021087 | VANDF |
| 4024101 | VANDF |
| C0540623 | UMLSCUI |
| CHEBI:7478 | CHEBI |
| CHEMBL1278 | ChEMBL_ID |
| CHEMBL1200601 | ChEMBL_ID |
| DB00952 | DRUGBANK_ID |
| C106783 | MESH_SUPPLEMENTAL_RECORD_UI |
| 4440 | PUBCHEM_CID |
| 45 | IUPHAR_LIGAND_ID |
| 7097 | INN_ID |
| QX3KXL1ZA2 | UNII |
| 141366 | RXNORM |
| 174286 | MMSL |
| 5157 | MMSL |
| d04285 | MMSL |
| 006605 | NDDF |
| 006606 | NDDF |
| 108408002 | SNOMEDCT_US |
| 108409005 | SNOMEDCT_US |
| 363571003 | SNOMEDCT_US |
| QX3KXL1ZA2 | INXIGHT DRUGS |
Pharmaceutical products:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| Naratriptan | HUMAN PRESCRIPTION DRUG LABEL | 1 | 0054-0278 | TABLET | 1 mg | ORAL | ANDA | 26 sections |
| Naratriptan | HUMAN PRESCRIPTION DRUG LABEL | 1 | 0054-0279 | TABLET | 2.50 mg | ORAL | ANDA | 26 sections |
| naratriptan | HUMAN PRESCRIPTION DRUG LABEL | 1 | 23155-054 | TABLET | 1 mg | ORAL | ANDA | 24 sections |
| naratriptan | HUMAN PRESCRIPTION DRUG LABEL | 1 | 23155-054 | TABLET | 1 mg | ORAL | ANDA | 24 sections |
| naratriptan | HUMAN PRESCRIPTION DRUG LABEL | 1 | 23155-055 | TABLET | 2.50 mg | ORAL | ANDA | 24 sections |
| naratriptan | HUMAN PRESCRIPTION DRUG LABEL | 1 | 23155-055 | TABLET | 2.50 mg | ORAL | ANDA | 24 sections |
| Naratriptan | HUMAN PRESCRIPTION DRUG LABEL | 1 | 69452-340 | TABLET, FILM COATED | 1 mg | ORAL | ANDA | 26 sections |
| Naratriptan | HUMAN PRESCRIPTION DRUG LABEL | 1 | 69452-341 | TABLET, FILM COATED | 2.50 mg | ORAL | ANDA | 26 sections |