Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H35N5O5 |
Molecular Weight | 581.6615 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C[C@@H](C=C2[C@H]1CC3=CNC4=C3C2=CC=C4)C(=O)N[C@]5(C)O[C@@]6(O)[C@@H]7CCCN7C(=O)[C@H](CC8=CC=CC=C8)N6C5=O
InChI
InChIKey=XCGSFFUVFURLIX-VFGNJEKYSA-N
InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1
Molecular Formula | C33H35N5O5 |
Molecular Weight | 581.6615 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/17149427
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17149427
The isolation and naming of ergotamine by Stoll occurred in 1925 but the complete elucidation of structure was not achieved until 1951, with synthesis following some 10 years later. Current sources of ergotamine include the isolation from field ergot and fermentation broth, as well as synthesis via coupling of (+)-lysergic acid with the appropriate synthetic peptidic moiety. Ergotamine was introduced into world commerce in 1921, and is currently marketed as its water soluble tartrate salt.
Ergotamine is a partial agonist at various tryptaminergic receptors (including the serotonin receptor [5-HT2]) and at various α-adrenergic receptors in blood vessels and various smooth muscles. It is likely that the major activity of ergotamine and related alkaloids is one of agonism at the 5-HT1B/1D receptors, just as with the “triptan” antimigraine compounds. FDA-labeled indications for ergotamine tartrate are in the abortion or prevention of vascular headaches, such as migraine, migraine variant, cluster headache, and histaminic cephalalgia.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17149427
Curator's Comment: In 1918 Arthur Stoll patented the isolation of ergotamine tartrate, which was subsequently marketed by Sandoz in 1921.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8397171 |
0.34 nM [Ki] | ||
Target ID: CHEMBL1898 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8397171 |
5.4 nM [Ki] | ||
Target ID: CHEMBL1983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8397171 |
0.4 nM [Ki] | ||
Target ID: CHEMBL2182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8397171 |
9.4 nM [Ki] | ||
Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11104741 |
3.0 nM [Ki] | ||
Target ID: CHEMBL2094251 |
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Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2881518 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ERGOMAR Approved UseErgomar® is indicated as therapy to abort or prevent vascular headache, e.g., migraine, migraine variants or a so-called "histaminic cephalalgia". Launch Date1983 |
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Primary | CAFERGOT Approved UseTreatment of acute attacks of migraine with or without aura in adults. |
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Sources: http://www.horizonpharma.com/migergot/ |
Primary | MIGERGOT Approved UseMIGERGOT is indicated as therapy to abort or prevent vascular headache, e.g., migraine, migraine variants or so-called “histaminic cephalalgia.” Ergotamine tartrate and caffeine suppositories should only be used for migraine headaches as they are not effective for other types of headaches and they lack analgesic properties. Launch Date1983 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
454 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3732370/ |
2 mg single, rectal dose: 2 mg route of administration: Rectal experiment type: SINGLE co-administered: |
ERGOTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
21.4 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3732370/ |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
ERGOTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1216 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3732370/ |
2 mg single, rectal dose: 2 mg route of administration: Rectal experiment type: SINGLE co-administered: |
ERGOTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
61 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3732370/ |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
ERGOTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4.38 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3932078/ |
3.89 μg/kg bw single, intravenous dose: 3.89 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
ERGOTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
2.04 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3932078/ |
1.94 μg/kg bw single, intravenous dose: 1.94 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
ERGOTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1.36 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3932078/ |
1.01 μg/kg bw single, intravenous dose: 1.01 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
ERGOTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.35 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3732370/ |
2 mg single, rectal dose: 2 mg route of administration: Rectal experiment type: SINGLE co-administered: |
ERGOTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2.15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3932078/ |
3.89 μg/kg bw single, intravenous dose: 3.89 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
ERGOTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
2.13 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3932078/ |
1.94 μg/kg bw single, intravenous dose: 1.94 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
ERGOTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
2.08 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3932078/ |
1.01 μg/kg bw single, intravenous dose: 1.01 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
ERGOTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
20 mg single, oral Overdose |
healthy, 21 |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea Sources: Vomiting (severe) Dizziness Blood pressure decreased Peripheral vasoconstriction Paresthesia Cyanosis peripheral Angina |
2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Disc. AE: Depression, Vertigo... AEs leading to discontinuation/dose reduction: Depression Sources: Vertigo Blurred vision Arrhythmia Hypersensitivity Migraine aggravated Urticaria Dyspnoea Fatigue Tachycardia Vagal reaction Dizziness Tinnitus |
2 mg single, oral Recommended |
unhealthy |
Disc. AE: Nausea, Lightheadedness... AEs leading to discontinuation/dose reduction: Nausea (2.4%) Sources: Lightheadedness (2.4%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Angina | Disc. AE | 20 mg single, oral Overdose |
healthy, 21 |
Blood pressure decreased | Disc. AE | 20 mg single, oral Overdose |
healthy, 21 |
Cyanosis peripheral | Disc. AE | 20 mg single, oral Overdose |
healthy, 21 |
Dizziness | Disc. AE | 20 mg single, oral Overdose |
healthy, 21 |
Nausea | Disc. AE | 20 mg single, oral Overdose |
healthy, 21 |
Paresthesia | Disc. AE | 20 mg single, oral Overdose |
healthy, 21 |
Peripheral vasoconstriction | Disc. AE | 20 mg single, oral Overdose |
healthy, 21 |
Vomiting | severe Disc. AE |
20 mg single, oral Overdose |
healthy, 21 |
Arrhythmia | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Blurred vision | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Depression | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Dizziness | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Dyspnoea | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Fatigue | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Hypersensitivity | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Migraine aggravated | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Tachycardia | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Tinnitus | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Urticaria | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Vagal reaction | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Vertigo | Disc. AE | 2 mg single, oral Recommended |
unhealthy, 40+/-10 |
Lightheadedness | 2.4% Disc. AE |
2 mg single, oral Recommended |
unhealthy |
Nausea | 2.4% Disc. AE |
2 mg single, oral Recommended |
unhealthy |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Ki 13 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | yes (co-administration study) Comment: Coadministration of ergotamine with potent CYP 3A4 inhibitors (ritonavir, nelfinavir, indinavir, erythromycin, clarithromycin, and troleandomycin) has been associated with acute ergot toxicity (ergotism) characterized by vasospasm and ischemia of the extremities |
PubMed
Title | Date | PubMed |
---|---|---|
[Severe generalized arteriospasm after a minimal therapeutic dose of ergotamine]. | 1972 Dec 14 |
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[Chronic ergotamine poisoning after migraine treatment]. | 1974 |
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[Ergotamine as a cause of arterial insufficiency]. | 1974 Oct 10 |
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Ergot-induced vasospasm of the lower extremities treated with epidural anaesthesia. | 1975 |
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[A case of hyposphygmia caused by ergotamine in migraine]. | 1975 Feb 21 |
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[Letter: Coronary spasm following ergotamine medication]. | 1975 Sep 5 |
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Reversal of ergotamine-induced arteriospasm by mechanical intra-arterial dilatation. | 1980 Dec 13 |
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[A case report of acute myocardial infarction induced by ergotamine tartrate (author's transl)]. | 1981 Mar |
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Myocardial infarction following administration of sublingual ergotamine. | 1982 Sep |
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[Ergotism causing peripheral arterial occlusion in the hand]. | 1983 Mar |
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Screening for new compounds with antiherpes activity. | 1984 Oct |
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[Ergotism with cerebral complications. Case report and review of the literature]. | 1986 Apr 5 |
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Amelioration of ergotamine withdrawal symptoms with naproxen. | 1987 Mar |
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Mitral and aortic valve disease associated with ergotamine therapy for migraine. Report of two cases and review of literature. | 1990 Jan |
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[Migraine caused by ergotamine tartrate dependence]. | 1992 Jul |
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Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype. | 1992 Jun 15 |
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[Daily chronic headache in patients with migraine induced by abuse of ergotamine-analgesics: response due to a protocol of outpatient treatment]. | 1993 Aug-Sep |
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Ergotamine-induced fetal stress: review of side effects of ergot alkaloids during pregnancy. | 1993 Sep |
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[Ergotamine-induced rectal lesions in asymptomatic patients]. | 1994 |
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Variant angina complicating ergot therapy of migraine. | 1994 Apr |
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Ergot induced peripheral vascular insufficiency, non-interventional treatment. | 1994 Mar |
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Ergotamine-induced headache can be sustained by sumatriptan daily intake. | 1994 Oct |
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Transcranial Doppler ultrasonographic features during drug withdrawal from drug-induced headache. A transcranial Doppler follow-up study. | 1998 Oct |
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Ergotamine-induced intermittent claudication. | 1999 May |
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Ventricular fibrillation secondary to ergotamine in a healthy young woman. | 1999 Oct |
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Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications. | 2000 Dec 5 |
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Acute tubulo-interstitial nephritis and renal infarction secondary to ergotamine therapy. | 2000 Nov |
|
Ergotamine, dihydroergotamine: current uses and problems. | 2001 |
|
Human 5-HT(5) receptors: the 5-HT(5A) receptor is functional but the 5-HT(5B) receptor was lost during mammalian evolution. | 2001 Apr 27 |
|
Ergotamine-induced acute vascular insufficiency of the lower limb--a case report. | 2001 Mar |
|
Successful treatment of threatening limb loss ischemia of the upper limb caused by ergotamine. A case report and review of the literature. | 2002 Apr |
|
Fibrotic valvular heart disease subsequent to bromocriptine treatment. | 2002 Nov-Dec |
|
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. | 2004 Aug |
|
[Transient global amnesia following the use of ergots in the treatment of migraine]. | 2004 Nov 16-30 |
|
Interactions of metoclopramide and ergotamine with human 5-HT(3A) receptors and human 5-HT reuptake carriers. | 2005 Oct |
|
Drug-induced fibrotic valvular heart disease. | 2009 Aug 15 |
|
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013 Sep 5 |
Patents
Sample Use Guides
MIGERGOT - ergotamine tartrate and caffeine rectal suppository.
One suppository at start of attack; second suppository after 1 hour, if needed for full relief. Two suppositories is the maximum dose for an individual attack.
Cafergot (Ergotamine tartrate 1 mg and Caffeine 100 mg Tablets)
First attack: The first time Cafergot is taken, an initial dose of 2 Cafergot tablets orally, is recommended. If relief is not obtained within half an hour, a further tablet should be administered; this may be repeated at half-hourly intervals, but the maximum daily dose of 6 tablets should not be exceeded. Subsequent attacks: If the pain persists, take 1 tablet every half an hour up to the maximum daily dose of 6 tablets. The maximum weekly dose is 10 tablets.
ERGOMAR SUBLINGUAL- ergotamine tartrate tablet
For best results, dosage should start at the first sign of an attack. Early Administration Gives Maximum Effectiveness. At the first sign of an attack or to relieve symptoms after onset of an attack, one 2 mg tablet is placed under the tongue. Another tablet should be taken at half-hour intervals thereafter, if necessary, but dosage must not exceed three tablets in any 24hour period. Total weekly dosage should not exceed five tablets (10 mg) in any one week. Ergomar® Sublingual Tablets should not be used for chronic daily administration.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3569604
The bovine anterior pituitary cells were implanted on culture tubes using D-valine minimal essential medium with serum to suppress the overgrowth of fibroblasts and then maintained in L-valine Dulbecco's modified Eagle medium. (3H)-Uridine uptake by these cells was suppressed by ergotamine at a concentration varing from 1-10 uM
Substance Class |
Chemical
Created
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admin
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Record UNII |
PR834Q503T
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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DEA NO. |
8676
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NDF-RT |
N0000007621
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NCI_THESAURUS |
C47794
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NDF-RT |
N0000007621
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WHO-ATC |
N02CA72
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WHO-VATC |
QN02CA52
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WHO-ATC |
N02CA02
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LIVERTOX |
363
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NDF-RT |
N0000175766
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WHO-ATC |
N02CA52
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WHO-VATC |
QN02CA02
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WHO-VATC |
QN02CA72
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1043
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391
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113-15-5
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C61751
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SUB06598MIG
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DB00696
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PR834Q503T
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Ergotamine
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95090
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PR834Q503T
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4025
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100000084579
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m4988
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8223
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4076
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ERGOTAMINE
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204-023-9
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CHEMBL442
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST |
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TARGET -> AGONIST |
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TARGET -> AGONIST |
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METABOLITE ACTIVE -> PARENT |
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PARENT -> IMPURITY |
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ACTIVE MOIETY |
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