ALMOTRIPTAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H25N3O2S
Molecular Weight	335.466
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCc1c[nH]c2ccc(cc12)CS(=O)(=O)N3CCCC3

InChI

InChIKey=WKEMJKQOLOHJLZ-UHFFFAOYSA-N

InChI=1S/C17H25N3O2S/c1-19(2)10-7-15-12-18-17-6-5-14(11-16(15)17)13-23(21,22)20-8-3-4-9-20/h5-6,11-12,18H,3-4,7-10,13H2,1-2H3

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021001s010s011lbl.pdf | https://www.drugs.com/cdi/almotriptan.html

endothelin (ETA, ETB); or tachykinin (NK1, NK2, NK3) binding sites.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition
Serotonin 1b (5-HT1b) receptor 37 Target ID: CHEMBL1898 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021001s008s009lbl.pdf	Agonist 2456	Migraine
Serotonin 1d (5-HT1d) receptor 46 Target ID: CHEMBL1983 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021001s010s011lbl.pdf	Agonist 2456	Migraine
Serotonin 1f (5-HT1f) receptor 11 Target ID: CHEMBL1805 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021001s010s011lbl.pdf	Agonist 2456	Migraine

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine 98 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021001s010s011lbl.pdf	Primary	Serotonin 1b (5-HT1b) receptor Serotonin 1d (5-HT1d) receptor Serotonin 1f (5-HT1f) receptor	Approved 7997	AXERT Approved Use Almotriptan tablets, USP are a 5HT1B/1D receptor agonist (triptan) indicated for: •Acute treatment of migraine attacks in adults with a history of migraine with or without aura (1.1) •Acute treatment of migraine headache pain in adolescents age 12 to 17 years with a history of migraine with or without aura, and who have migraine attacks usually lasting 4 hours or more (1.1) Important Limitations: •Use only after a clear diagnosis of migraine has been established (1.2) •In adolescents age 12 to 17 years, efficacy of almotriptan tablets on migraine-associated symptoms was not established (1.2) •Not intended for the prophylactic therapy of migraine (1.2) •Not indicated for the treatment of cluster headache (1.2) 1.1 Acute Treatment of Migraine Attacks Adults Almotriptan tablets, USP are indicated for the acute treatment of migraine attacks in patients with a history of migraine with or without aura. Adolescents Age 12 to 17 Years Almotriptan tablets are indicated for the acute treatment of migraine headache pain in patients with a history of migraine attacks with or without aura usually lasting 4 hours or more (when untreated). 1.2 Important Limitations Almotriptan tablets should only be used where a clear diagnosis of migraine has been established. If a patient has no response for the first migraine attack treated with almotriptan tablets, the diagnosis of migraine should be reconsidered before almotriptan tablets are administered to treat any subsequent attacks. In adolescents age 12 to 17 years, efficacy of almotriptan tablets on migraine-associated symptoms (nausea, photophobia, and phonophobia) was not established. Almotriptan tablets are not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine [see Contraindications (4.7) Launch Date 989193600000

C_max

Value	Dose	Co-administered	Analyte	Population
52.6 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12723463	12.5 mg single, oral dose: 12.5 mg route of administration: Oral experiment type: SINGLE co-administered:		ALMOTRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
312 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12723463	12.5 mg single, oral dose: 12.5 mg route of administration: Oral experiment type: SINGLE co-administered:		ALMOTRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.1 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12723463	12.5 mg single, oral dose: 12.5 mg route of administration: Oral experiment type: SINGLE co-administered:		ALMOTRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021001s015lbl.pdf	unknown, oral		ALMOTRIPTAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
65% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021001s015lbl.pdf	unknown, oral		ALMOTRIPTAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
3 mg single, intravenous Dose: 3 mg Route: intravenous Route: single Dose: 3 mg Sources: https://pubmed.ncbi.nlm.nih.gov/12463724	healthy, 19-33 years Health Status: healthy Age Group: 19-33 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/12463724	Sources: https://pubmed.ncbi.nlm.nih.gov/12463724
10 mg single, subcutaneous Highest studied dose Dose: 10 mg Route: subcutaneous Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/11768838	unhealthy, 42 years (range: 18-72 years) Health Status: unhealthy Age Group: 42 years (range: 18-72 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11768838	Sources: https://pubmed.ncbi.nlm.nih.gov/11768838
12.5 mg multiple, oral Recommended Dose: 12.5 mg Route: oral Route: multiple Dose: 12.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/12005273	unhealthy, 42 years (range: 18-72 years) Health Status: unhealthy Age Group: 42 years (range: 18-72 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12005273	Disc. AE: Chest pain, Electrocardiogram QTc interval prolonged... AEs leading to discontinuation/dose reduction: Chest pain (0.9%) Electrocardiogram QTc interval prolonged (0.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/12005273
100 mg multiple, oral Highest studied dose Dose: 100 mg Route: oral Route: multiple Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_prntlbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_prntlbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_prntlbl.pdf
200 mg single, oral Highest studied dose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_prntlbl.pdf	healthy, adult Health Status: healthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_prntlbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_prntlbl.pdf

AEs

AE	Significance	Dose	Population
Electrocardiogram QTc interval prolonged	0.7% Disc. AE	12.5 mg multiple, oral Recommended Dose: 12.5 mg Route: oral Route: multiple Dose: 12.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/12005273	unhealthy, 42 years (range: 18-72 years) Health Status: unhealthy Age Group: 42 years (range: 18-72 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12005273
Chest pain	0.9% Disc. AE	12.5 mg multiple, oral Recommended Dose: 12.5 mg Route: oral Route: multiple Dose: 12.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/12005273	unhealthy, 42 years (range: 18-72 years) Health Status: unhealthy Age Group: 42 years (range: 18-72 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12005273

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1470	inhibitor 1318	substrate 1038 inhibitor 1421

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1268 CYP2A6 594 CYP2B6 679 CYP2C19 1215 CYP2E1 761 CYP3A4/5 225 CYP4A9/11 30	FMO3 49 CYP3A4/5 68 CYP1A2 892 CYP2C8 586 CYP2C19 830

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1406	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 49	no
CYP2A6 625	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 49	no
CYP2B6 845	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 49	no
CYP2C19 1277	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 49	no
CYP2C9 1362	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 49	no
CYP2E1 841	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 49	no
CYP3A4/5 277	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 49	no
CYP4A9/11 30	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 49	no
CYP2D6 1455	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 49	weak [Ki 87 uM]

Drug as victim

Target	Modality	Activity
CYP1A2 892	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 27	yes
CYP2C19 830	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 27	yes
CYP2C8 586	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 27	yes
CYP2D6 1038	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 27	yes
CYP3A4 1470	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 27, 49	yes
CYP3A4/5 68	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 27	yes
FMO3 49	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21001_Axert_pharmr_P1.pdf Page: 27	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:520985	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:520985
ZINC	ZINC000000018087	http://zinc15.docking.org/substances/ZINC000000018087

PubMed

Title	Date	PubMed
Comparative aspects of triptans in treating migraine.	2001	12739316
Lack of pharmacokinetic interaction between the antimigraine compound, almotriptan, and propranolol in healthy volunteers.	2001 Feb	11298665
Evaluation of the potential pharmacokinetic interaction between almotriptan and fluoxetine in healthy volunteers.	2001 Feb	11210405
[Migraine headache. Severe attacks: triptans are essential].	2001 Jul 19	11499152
Acute treatment of migraine and the role of triptans.	2001 Mar	11898508
Hemodynamic and electrocardiographic effects of almotriptan in healthy volunteers.	2001 Mar	11243418
Efficacy and tolerability of subcutaneous almotriptan for the treatment of acute migraine: a randomized, double-blind, parallel-group, dose-finding study.	2001 Nov	11768838
Dose finding, placebo-controlled study of oral almotriptan in the acute treatment of migraine.	2001 Nov 27	11723269
Gateways to clinical trials.	2002 Dec	12616965
A long-term open-label study of oral almotriptan 12.5 mg for the treatment of acute migraine.	2002 Jan	12005273
Within-patient early versus delayed treatment of migraine attacks with almotriptan: the sooner the better.	2002 Jan	12005272
[Treatment of migraine in patients with hypertension and ischemic heart disease].	2002 Jan 20	12122940
A review of the effects of almotriptan and other triptans on clinical trial outcomes that are meaningful to patients with migraine.	2003 Feb	12749502
[Almotriptan in the treatment of migraine attacks in clinical practice: results of the TEA 2000 observational study].	2003 Jan-Feb	12590376
Almotriptan versus rizatriptan in patients with migraine in Spain.	2003 Jul-Aug	12890128
Cost-effectiveness of almotriptan and rizatriptan in the treatment of acute migraine.	2003 Nov	14693315
Gateways to clinical trials.	2004 Jan-Feb	14988742
Evaluating triptan usage: a rebuttal.	2004 Oct	15447710
Pharmacokinetics and safety of oral almotriptan in healthy male volunteers.	2004 Oct	15386481
Priorities for triptan treatment attributes and the implications for selecting an oral triptan for acute migraine: a study of US primary care physicians (the TRIPSTAR Project).	2004 Sep	15531016
Correlation between lipophilicity and triptan outcomes.	2005 Jan	15663606

Patents

Sample Use Guides

In Vivo Use Guide

Adults and adolescents age 12 to 17 years: 6.25 mg or 12.5 mg single

Route of Administration: Oral

In Vitro Use Guide

In vitro Almotriptan showed selectivity of action for migraine-related human arteries (i.e. contractile EC(50) of 30 and 700 nm for meningeal and temporal arteries, respectively), whereas the effect on arteries supplying blood to the brain was lower.

Name

Type

Language

ALMOTRIPTAN

Official Name

English

1-(((3-(2-(DIMETHYLAMINO)ETHYL)INDOL-5-YL)METHYL)SULFONYL)PYRROLIDINE

Systematic Name

English

ALMOTRIPTAN [USAN]

Common Name

English

ALMOTRIPTAN [INN]

Common Name

English

LAS-31416

Code

English

LAS 31416

Code

English

ALMOTRIPTAN [VANDF]

Common Name

English

ALMOTRIPTAN [WHO-DD]

Common Name

English

ALMOTRIPTAN [MI]

Common Name

English

PYRROLIDINE, 1-(((3-(2-(DIMETHYLAMINO)ETHYL)-1H-INDOL-5-YL)METHYL)SULFONYL)-

Systematic Name

English

NSC-760092

Code

English

Classification Tree Code System Code

WHO-VATC

QN02CC05