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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H34O2
Molecular Weight 318.4935
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SEPRANOLONE

SMILES

[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])C[C@@H](O)CC[C@]34C

InChI

InChIKey=AURFZBICLPNKBZ-FZCSVUEKSA-N
InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15-,16-,17+,18-,19-,20-,21+/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H34O2
Molecular Weight 318.4935
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Sepranolone (UC1010) is a GABA-A modulating steroid antagonist (GAMSA) and does not antagonize the effect of GABA itself or other GABAA agonists like benzodiazepines and barbiturates. The interaction of neuroactive steroids (i.e., allopregnanolone and Sepranolone) with GABA-A receptor is particularly important in mood disorders. For example, allopregnanolone administration decreased saccadic eye velocity in healthy female volunteers and induced sedation and these effects were diminished by simultaneous sepranolone administration. Thus, allopregnanolone effects are antagonized by its isomer sepranolone. UC1010 reduces symptom severity and impairment significantly more efficiently than placebo in women with a well-defined, pure premenstrual dysphoric disorder. No severe adverse events were reported during the UC1010 treatment and safety parameters (vital signs and blood chemistry) remained normal during the study. It was revealed also that increases in ring A-reduced progesterone metabolites, particularly Sepranolone, are associated with chronic fatigue syndrome.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.7 µM [IC50]
Target ID: P18507
Gene ID: 2566.0
Gene Symbol: GABRG2
Target Organism: Homo sapiens (Human)
2.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
143 nM
0.2 mg/kg 1 times / day single, intravenous
dose: 0.2 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SEPRANOLONE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
21009 nM × min
0.2 mg/kg 1 times / day single, intravenous
dose: 0.2 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SEPRANOLONE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
847 min
0.2 mg/kg 1 times / day single, intravenous
dose: 0.2 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SEPRANOLONE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

5 injections -10 or 16 mg
Route of Administration: Other
Sepranolone from 1 uM to 1 mM does not affect baseline Cl(-) uptake in rat cortical homogenates. Neither does Sepranolone at dose range of 100 nM to 100 uM interact with 10 uM GABA in the Cl(-) uptake assay. In addition, Sepranolone at the dose range of 1-30 uM does not affect flunitrazepam and pentobarbital-induced increase of Cl(-) uptake. We conclude that Sepranolone selectively inhibits the allopregnanolone-induced Cl(-) uptake with respect to allopregnanolone concentrations. The IC(50) of Sepranolone inhibition on 1 uM allopregnanolone-induced Cl(-) uptake was calculated to be 12.25 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 03:59:37 GMT 2023
Edited
by admin
on Sat Dec 16 03:59:37 GMT 2023
Record UNII
3P8Z6V53MU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SEPRANOLONE
INN  
INN  
Official Name English
NSC-97078
Code English
3.BETA.-HYDROXY-5.ALPHA.-TETRAHYDROPROGESTERONE
Common Name English
ALLOPREGNAN-3.BETA.-OL-20-ONE [MI]
Common Name English
U-0949
Code English
UC1010
Code English
ISOALLOPREGNANOLONE
Common Name English
EPIALLOPREGNANOLONE
Common Name English
sepranolone [INN]
Common Name English
3.BETA.-HYDROXY-5.ALPHA.-PREGNAN-20-ONE
Systematic Name English
ISOPREGNANOLONE
Common Name English
UC-1010
Code English
PREGNAN-20-ONE, 3-HYDROXY-, (3.BETA.,5.ALPHA.)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C776
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
Code System Code Type Description
DRUG BANK
DB12972
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY
WIKIPEDIA
ISOPREGNANOLONE
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID001023710
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY
FDA UNII
3P8Z6V53MU
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY
MERCK INDEX
m1538
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C152338
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY
PUBCHEM
92787
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY
SMS_ID
100000127636
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY
EVMPD
SUB33700
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY
INN
9618
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY
NSC
97078
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-224-2
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY
CAS
516-55-2
Created by admin on Sat Dec 16 03:59:37 GMT 2023 , Edited by admin on Sat Dec 16 03:59:37 GMT 2023
PRIMARY
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