U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H25NO4S.ClH
Molecular Weight 435.964
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADROGOLIDE HYDROCHLORIDE

SMILES

Cl.[H][C@@]12CCC3=CC(OC(C)=O)=C(OC(C)=O)C=C3[C@@]1([H])C4=C(CN2)SC(CCC)=C4

InChI

InChIKey=NPEZSCRKHFTLPE-MYXGOWFTSA-N
InChI=1S/C22H25NO4S.ClH/c1-4-5-15-9-17-21(28-15)11-23-18-7-6-14-8-19(26-12(2)24)20(27-13(3)25)10-16(14)22(17)18;/h8-10,18,22-23H,4-7,11H2,1-3H3;1H/t18-,22+;/m1./s1

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C22H25NO4S
Molecular Weight 399.503
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 51.0 nM [Ki]
Agonist
2678
 15.0 nM [Ki]
Agonist
2678
 750.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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/
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/
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
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
Doses

Doses

DosePopulationAdverse events​
20 mg single, intravenous (max)
Studied dose
Dose: 20 mg
Route: intravenous
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
unhealthy, ADULT
n = 13
Health Status: unhealthy
Condition: Parkinson disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
Disc. AE: Nausea and vomiting...
Other AEs: Asthenia, Nausea...
AEs leading to
discontinuation/dose reduction:
Nausea and vomiting (severe, 1 pt)
Other AEs:
Asthenia (62%)
Nausea (38%)
headache (62%)
vomiting (31%)
Postural hypotension (31%)
injection site reaction (85%)
vasodilatation (31%)
Dizziness (31%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
40 mg 1 times / day multiple, intravenous (unknown)
Highest studied dose
Dose: 40 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10360765
unhealthy
n = 14
Health Status: unhealthy
Condition: Parkinson disease
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
https://pubmed.ncbi.nlm.nih.gov/10360765
Other AEs: headache, Flushing...
Other AEs:
headache
Flushing
Nausea
Injection site reaction
Sources:
https://pubmed.ncbi.nlm.nih.gov/10360765
AEs

AEs

AESignificanceDosePopulation
Dizziness 31%
20 mg single, intravenous (max)
Studied dose
Dose: 20 mg
Route: intravenous
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
unhealthy, ADULT
n = 13
Health Status: unhealthy
Condition: Parkinson disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
Postural hypotension 31%
20 mg single, intravenous (max)
Studied dose
Dose: 20 mg
Route: intravenous
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
unhealthy, ADULT
n = 13
Health Status: unhealthy
Condition: Parkinson disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
vasodilatation 31%
20 mg single, intravenous (max)
Studied dose
Dose: 20 mg
Route: intravenous
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
unhealthy, ADULT
n = 13
Health Status: unhealthy
Condition: Parkinson disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
vomiting 31%
20 mg single, intravenous (max)
Studied dose
Dose: 20 mg
Route: intravenous
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
unhealthy, ADULT
n = 13
Health Status: unhealthy
Condition: Parkinson disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
Nausea 38%
20 mg single, intravenous (max)
Studied dose
Dose: 20 mg
Route: intravenous
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
unhealthy, ADULT
n = 13
Health Status: unhealthy
Condition: Parkinson disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
Asthenia 62%
20 mg single, intravenous (max)
Studied dose
Dose: 20 mg
Route: intravenous
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
unhealthy, ADULT
n = 13
Health Status: unhealthy
Condition: Parkinson disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
headache 62%
20 mg single, intravenous (max)
Studied dose
Dose: 20 mg
Route: intravenous
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
unhealthy, ADULT
n = 13
Health Status: unhealthy
Condition: Parkinson disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
injection site reaction 85%
20 mg single, intravenous (max)
Studied dose
Dose: 20 mg
Route: intravenous
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
unhealthy, ADULT
n = 13
Health Status: unhealthy
Condition: Parkinson disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
Nausea and vomiting severe, 1 pt
Disc. AE
20 mg single, intravenous (max)
Studied dose
Dose: 20 mg
Route: intravenous
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
unhealthy, ADULT
n = 13
Health Status: unhealthy
Condition: Parkinson disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/11607045
Flushing
40 mg 1 times / day multiple, intravenous (unknown)
Highest studied dose
Dose: 40 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10360765
unhealthy
n = 14
Health Status: unhealthy
Condition: Parkinson disease
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
https://pubmed.ncbi.nlm.nih.gov/10360765
Injection site reaction
40 mg 1 times / day multiple, intravenous (unknown)
Highest studied dose
Dose: 40 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10360765
unhealthy
n = 14
Health Status: unhealthy
Condition: Parkinson disease
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
https://pubmed.ncbi.nlm.nih.gov/10360765
Nausea
40 mg 1 times / day multiple, intravenous (unknown)
Highest studied dose
Dose: 40 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10360765
unhealthy
n = 14
Health Status: unhealthy
Condition: Parkinson disease
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
https://pubmed.ncbi.nlm.nih.gov/10360765
headache
40 mg 1 times / day multiple, intravenous (unknown)
Highest studied dose
Dose: 40 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10360765
unhealthy
n = 14
Health Status: unhealthy
Condition: Parkinson disease
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
https://pubmed.ncbi.nlm.nih.gov/10360765
Sourcing

Sourcing

Vendor/AggregatorIDURL
Compound Cloud
176876
Compound Cloud
6918298
MuseChem
I001236
https://www.musechem.com/product/I001236.html
MuseChem
M127354
https://www.musechem.com/product/M127354.html
PubMed

PubMed

TitleDatePubMed
(5aR,11bS)-4,5,5a,6,7,11b-hexahydro-2-propyl-3-thia-5-azacyclopent-1- ena[c]-phenanthrene-9,10-diol (A-86929): a potent and selective dopamine D1 agonist that maintains behavioral efficacy following repeated administration and characterization of its diacetyl prodrug (ABT-431).
1995 Sep 1
Hyperactivity and behavioral seizures in rodents following treatment with the dopamine D1 receptor agonists A-86929 and ABT-431.
1996 Dec 19
ABT-431: the diacetyl prodrug of A-86929, a potent and selective dopamine D1 receptor agonist: in vitro characterization and effects in animal models of Parkinson's disease.
1996 Jan
ABT-431, a D1 receptor agonist prodrug, has efficacy in Parkinson's disease.
1999 Jun
Effect of a selective dopamine D1 agonist (ABT-431) on smoked cocaine self-administration in humans.
1999 Mar
Patents

Patents

CA2461586A1
7
US20060030607
4

Sample Use Guides

In Vivo Use Guide
2, 4 mg over a 1-h period immediately prior to cocaine self-administration sessions
Route of Administration: Intravenous
In Vitro Use Guide
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 Fri Dec 15 16:03:14 GMT 2023
Edited
by admin
on Fri Dec 15 16:03:14 GMT 2023
Record UNII
69MG3OZA0H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ADROGOLIDE HYDROCHLORIDE
USAN  
USAN  
Official Name English
ADROGOLIDE HCL
Common Name English
BENZO(F)THIENO(2,3-C)QUINOLINE-9,10-DIOL, 4,5,5A,6,7,11B-HEXAHYDRO-2-PROPYL-, DIACETATE (ESTER), HYDROCHLORIDE, (5AR-TRANS)-
Common Name English
ADROGOLIDE HYDROCHLORIDE [USAN]
Common Name English
(5aR,11bS)-4,5,5a,6,7,11b-Hexahydro-2-propylbenzo[f]thieno[2,3-c]quinoline-9,10-diol diacetate (ester), hydrochloride
Common Name English
A-93431.1
Code English
ABT-431
Code English
Classification Tree Code System Code
NCI_THESAURUS C66884
Created by admin on Fri Dec 15 16:03:14 GMT 2023 , Edited by admin on Fri Dec 15 16:03:14 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL2104655
Created by admin on Fri Dec 15 16:03:14 GMT 2023 , Edited by admin on Fri Dec 15 16:03:14 GMT 2023
PRIMARY
FDA UNII
69MG3OZA0H
Created by admin on Fri Dec 15 16:03:14 GMT 2023 , Edited by admin on Fri Dec 15 16:03:14 GMT 2023
PRIMARY
USAN
KK-32
Created by admin on Fri Dec 15 16:03:14 GMT 2023 , Edited by admin on Fri Dec 15 16:03:14 GMT 2023
PRIMARY
MESH
C095428
Created by admin on Fri Dec 15 16:03:14 GMT 2023 , Edited by admin on Fri Dec 15 16:03:14 GMT 2023
PRIMARY
PUBCHEM
6918298
Created by admin on Fri Dec 15 16:03:14 GMT 2023 , Edited by admin on Fri Dec 15 16:03:14 GMT 2023
PRIMARY
NCI_THESAURUS
C72681
Created by admin on Fri Dec 15 16:03:14 GMT 2023 , Edited by admin on Fri Dec 15 16:03:14 GMT 2023
PRIMARY
CAS
166591-11-3
Created by admin on Fri Dec 15 16:03:14 GMT 2023 , Edited by admin on Fri Dec 15 16:03:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID40937220
Created by admin on Fri Dec 15 16:03:14 GMT 2023 , Edited by admin on Fri Dec 15 16:03:14 GMT 2023
PRIMARY
Related Record Type Details
Structure of ADROGOLIDE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of A-86929 MONOACETATE 1 HYDROCHLORIDE
IMPURITY -> PARENT
Structure of A-86929 MONOACETATE 2 HYDROCHLORIDE
IMPURITY -> PARENT
Structure of A-86929 HYDROCHLORIDE
IMPURITY -> PARENT
Related Record Type Details
Structure of ADROGOLIDE
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