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Details

Stereochemistry ABSOLUTE
Molecular Formula C3H6N2O2
Molecular Weight 102.0919
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOSERINE

SMILES

N[C@@H]1CONC1=O

InChI

InChIKey=DYDCUQKUCUHJBH-UWTATZPHSA-N
InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1

HIDE SMILES / InChI

Molecular Formula C3H6N2O2
Molecular Weight 102.0919
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cycloserine was discovered simultaneously in 1954 by Eli Lilly and Merck. The drug was approved for the treatment of active pulmonary and extrapulmonary tuberculosis and marketed under the name Seromycin (among the others). Cycloserine suppresses the synthesis of bacterial wall by inhibitin two enzymes: alanine racemase and d-alanine ligase.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SEROMYCIN

Cmax

ValueDoseCo-administeredAnalytePopulation
42.92 mg/L
500 mg single, oral
D-CYCLOSERINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
643.29 mg × h/L
500 mg single, oral
D-CYCLOSERINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
13.27 h
500 mg single, oral
D-CYCLOSERINE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
The usual dosage is 500 mg to 1 g daily in divided doses monitored by blood levels. The initial adult dosage most frequently given is 250 mg twice daily at 12–hour intervals for the first 2 weeks. A daily dosage of 1 g should not be exceeded.
Route of Administration: Oral
In Vitro Use Guide
Multidrug resistant Mycobacterium tuberculosis isolates were incubated with 20 uL of cycloserine. 5 different cycloserine concentrations (8, 16, 32, 64, and > 64 ug/mL).
Substance Class Chemical
Record UNII
95IK5KI84Z
Record Status Validated (UNII)
Record Version