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
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
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28319848 |
1.7 µM [IC50] | ||
Target ID: P18507 Gene ID: 2566.0 Gene Symbol: GABRG2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18430052 |
2.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
143 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18949461 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21009 nM × min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18949461 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
847 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18949461 |
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28319848
5 injections -10 or 16 mg
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12915239
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
Edited
Sat Dec 16 03:59:37 GMT 2023
by
admin
on
Sat Dec 16 03:59:37 GMT 2023
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Record UNII |
3P8Z6V53MU
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C776
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DB12972
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ISOPREGNANOLONE
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m1538
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C152338
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92787
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TARGET->NEGATIVE ALLOSTERIC MODULATOR (NAM) |
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ACTIVE MOIETY |
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