Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H21NO2S |
Molecular Weight | 315.43 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC1=CC2=C(CN[C@@H]3CCC4=CC(O)=C(O)C=C4[C@@H]23)S1
InChI
InChIKey=REHAKLRYABHSQJ-KDOFPFPSSA-N
InChI=1S/C18H21NO2S/c1-2-3-11-7-13-17(22-11)9-19-14-5-4-10-6-15(20)16(21)8-12(10)18(13)14/h6-8,14,18-21H,2-5,9H2,1H3/t14-,18+/m1/s1
Molecular Formula | C18H21NO2S |
Molecular Weight | 315.43 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11607045Curator's Comment: description was created based on several sources, including:
http://adisinsight.springer.com/drugs/800006590 | https://www.ncbi.nlm.nih.gov/pubmed/8558425 | https://www.ncbi.nlm.nih.gov/pubmed/10360765
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607045
Curator's Comment: description was created based on several sources, including:
http://adisinsight.springer.com/drugs/800006590 | https://www.ncbi.nlm.nih.gov/pubmed/8558425 | https://www.ncbi.nlm.nih.gov/pubmed/10360765
Adrogolide is a chemically stable prodrug of the dopamine D1 receptor agonist A-86929. Adrogolide is rapidly converted in plasma to A-86929. A-86929 has high affinity and functional selectivity for the dopamine D1 receptor. Adrogolide has been in phase II clinical trials for the treatment of Parkinson's disease and cocaine abuse. However, this research has been discontinued. The adverse events associated with its use of adrogolide were of mild-to-moderate severity and included injection site reaction, asthenia, headache, nausea, vomiting, postural hypotension, vasodilitation, and dizziness.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2056 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607045 |
51.0 nM [Ki] | ||
Target ID: CHEMBL1850 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607045 |
15.0 nM [Ki] | ||
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607045 |
750.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
19.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
19.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
6.6 mg single, respiratory dose: 6.6 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
13.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
19.8 mg single, respiratory dose: 19.8 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
15.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
3.3 mg 1 times / day single, respiratory dose: 3.3 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
24.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
13.2 mg single, respiratory dose: 13.2 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
16.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
6.6 mg single, respiratory dose: 6.6 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
22.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
19.8 mg single, respiratory dose: 19.8 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
10.6 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
3.3 mg 1 times / day single, respiratory dose: 3.3 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
26 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
13.2 mg single, respiratory dose: 13.2 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
6.6 mg single, respiratory dose: 6.6 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
19.8 mg single, respiratory dose: 19.8 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
3.3 mg 1 times / day single, respiratory dose: 3.3 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10564839/ |
13.2 mg single, respiratory dose: 13.2 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
A-86929 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
20 mg single, intravenous Studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Nausea and vomiting... Other AEs: injection site reaction, vomiting... AEs leading to discontinuation/dose reduction: Nausea and vomiting (severe, 1 pt) Other AEs:injection site reaction (85%) Sources: vomiting (31%) Nausea (38%) headache (62%) Asthenia (62%) Postural hypotension (31%) vasodilatation (31%) Dizziness (31%) |
40 mg 1 times / day multiple, intravenous Highest studied dose Dose: 40 mg, 1 times / day Route: intravenous Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: headache, Flushing... Other AEs: headache Sources: Flushing Nausea Injection site reaction |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dizziness | 31% | 20 mg single, intravenous Studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Postural hypotension | 31% | 20 mg single, intravenous Studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
vasodilatation | 31% | 20 mg single, intravenous Studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
vomiting | 31% | 20 mg single, intravenous Studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Nausea | 38% | 20 mg single, intravenous Studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Asthenia | 62% | 20 mg single, intravenous Studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
headache | 62% | 20 mg single, intravenous Studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
injection site reaction | 85% | 20 mg single, intravenous Studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Nausea and vomiting | severe, 1 pt Disc. AE |
20 mg single, intravenous Studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Flushing | 40 mg 1 times / day multiple, intravenous Highest studied dose Dose: 40 mg, 1 times / day Route: intravenous Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
|
Injection site reaction | 40 mg 1 times / day multiple, intravenous Highest studied dose Dose: 40 mg, 1 times / day Route: intravenous Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
|
Nausea | 40 mg 1 times / day multiple, intravenous Highest studied dose Dose: 40 mg, 1 times / day Route: intravenous Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
|
headache | 40 mg 1 times / day multiple, intravenous Highest studied dose Dose: 40 mg, 1 times / day Route: intravenous Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10227086
2, 4 mg over a 1-h period immediately prior to cocaine self-administration sessions
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607045
The EC50 value of A-86929 at cloned human dopamine D1 receptors was more than 400 times greater than that observed at the cloned human dopamine D2 receptor, and the potency of A-86929 was nearly 10-fold greater at the human dopamine D5 than at the dopamine D1 receptor.
Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Apr 01 20:53:23 GMT 2025
by
admin
on
Tue Apr 01 20:53:23 GMT 2025
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Record UNII |
S3ZIH99X6E
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Record Status |
Validated (UNII)
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Record Version |
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-
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DTXSID501028589
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171961-95-8
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admin on Tue Apr 01 20:53:23 GMT 2025 , Edited by admin on Tue Apr 01 20:53:23 GMT 2025
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A-86929
Created by
admin on Tue Apr 01 20:53:23 GMT 2025 , Edited by admin on Tue Apr 01 20:53:23 GMT 2025
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9841398
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187661-43-4
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admin on Tue Apr 01 20:53:23 GMT 2025 , Edited by admin on Tue Apr 01 20:53:23 GMT 2025
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NON-SPECIFIC STEREOCHEMISTRY | |||
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S3ZIH99X6E
Created by
admin on Tue Apr 01 20:53:23 GMT 2025 , Edited by admin on Tue Apr 01 20:53:23 GMT 2025
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
AGONIST
Ki
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST |
AGONIST
EC50
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Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
---|---|---|---|---|
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ACTIVE MOIETY |