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

Details

Stereochemistry ABSOLUTE
Molecular Formula C3H6N2O2
Molecular Weight 102.0921
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOSERINE

SMILES

C1[C@]([H])(C(=NO1)O)N

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

Description
Curator's Comment:: description was created based on several sources, including ISBN-13: 978-0199337149

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.

Originator

Sources: ISBN-13: 978-0199337149
Curator's Comment:: # Eli Lilly and Merck

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SEROMYCIN

Approved Use

Seromycin is indicated in the treatment of active pulmonary and extrapulmonary tuberculosis (including renal disease) when the causative organisms are susceptible to this drug and when treatment with the primary medications (streptomycin, isoniazid, rifampin, and ethambutol) has proved inadequate.

Launch Date

-1.73836796E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
42.92 mg/L
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
D-CYCLOSERINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
643.29 mg × h/L
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
D-CYCLOSERINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.27 h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
D-CYCLOSERINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
1000 mg single, oral
Recommended
Dose: 1000 mg
Route: oral
Route: single
Dose: 1000 mg
Sources: Page: p.7
healthy, 4.2
n = 12
Health Status: healthy
Age Group: 4.2
Sex: M+F
Population Size: 12
Sources: Page: p.7
250 mg 2 times / day multiple, oral
Recommended
Dose: 250 mg, 2 times / day
Route: oral
Route: multiple
Dose: 250 mg, 2 times / day
Sources: Page: p.7
healthy, 4.2
n = 12
Health Status: healthy
Age Group: 4.2
Sex: M+F
Population Size: 12
Sources: Page: p.7
50 mg 1 times / week multiple, oral
Dose: 50 mg, 1 times / week
Route: oral
Route: multiple
Dose: 50 mg, 1 times / week
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Nicotine dependence
Population Size: 30
Sources:
Other AEs: Anorexia, Dizziness...
Other AEs:
Anorexia (below serious, 4 patients)
Dizziness (below serious, 4 patients)
Restlessness (below serious, 7 patients)
Sore throat (below serious, 6 patients)
Urticaria (below serious, 5 patients)
Sources:
50 mg single, oral
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy
n = 34
Health Status: unhealthy
Condition: Autism Spectrum Disorders
Population Size: 34
Sources:
Other AEs: Headache, Vomiting...
Other AEs:
Headache (below serious, 9 patients)
Vomiting (below serious, 6 patients)
Irritability (below serious, 16 patients)
Feeling sad (below serious, 5 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Anorexia below serious, 4 patients
50 mg 1 times / week multiple, oral
Dose: 50 mg, 1 times / week
Route: oral
Route: multiple
Dose: 50 mg, 1 times / week
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Nicotine dependence
Population Size: 30
Sources:
Dizziness below serious, 4 patients
50 mg 1 times / week multiple, oral
Dose: 50 mg, 1 times / week
Route: oral
Route: multiple
Dose: 50 mg, 1 times / week
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Nicotine dependence
Population Size: 30
Sources:
Urticaria below serious, 5 patients
50 mg 1 times / week multiple, oral
Dose: 50 mg, 1 times / week
Route: oral
Route: multiple
Dose: 50 mg, 1 times / week
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Nicotine dependence
Population Size: 30
Sources:
Sore throat below serious, 6 patients
50 mg 1 times / week multiple, oral
Dose: 50 mg, 1 times / week
Route: oral
Route: multiple
Dose: 50 mg, 1 times / week
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Nicotine dependence
Population Size: 30
Sources:
Restlessness below serious, 7 patients
50 mg 1 times / week multiple, oral
Dose: 50 mg, 1 times / week
Route: oral
Route: multiple
Dose: 50 mg, 1 times / week
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Nicotine dependence
Population Size: 30
Sources:
Irritability below serious, 16 patients
50 mg single, oral
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy
n = 34
Health Status: unhealthy
Condition: Autism Spectrum Disorders
Population Size: 34
Sources:
Feeling sad below serious, 5 patients
50 mg single, oral
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy
n = 34
Health Status: unhealthy
Condition: Autism Spectrum Disorders
Population Size: 34
Sources:
Vomiting below serious, 6 patients
50 mg single, oral
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy
n = 34
Health Status: unhealthy
Condition: Autism Spectrum Disorders
Population Size: 34
Sources:
Headache below serious, 9 patients
50 mg single, oral
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy
n = 34
Health Status: unhealthy
Condition: Autism Spectrum Disorders
Population Size: 34
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Spectrum of drugs against atypical mycobacteria: how valid is the current practice of drug susceptibility testing and the choice of drugs?
1992 Dec
Selective susceptibility of transformed T lymphocytes to induction of apoptosis by PSC 833, an inhibitor of P-glycoprotein.
2001
Pathological apoptosis by xanthurenic acid, a tryptophan metabolite: activation of cell caspases but not cytoskeleton breakdown.
2001
[A case of drug-resistant pulmonary tuberculosis treated successfully following disappearance of rifampicin resistance after 17 years' chemotherapy].
2001 Apr
Role of specific aminotransferases in de novo glutamate synthesis and redox shuttling in the retina.
2001 Dec 1
Cycloserine fatty acid derivatives as prodrugs: synthesis, degradation and in vitro skin permeability.
2002 Apr
A case series of D-cycloserine added to donepezil in the treatment of Alzheimer's disease.
2002 Fall
Impaired visual memory in rats reared in isolation is reversed by D-cycloserine in the adult rat.
2002 Feb 15
Substrate-reduction therapy enhances the benefits of bone marrow transplantation in young mice with globoid cell leukodystrophy.
2002 Jan
[Pharmacological support of exposure therapy in anxiety disorders. Animal experiment studies].
2002 May
Molecular epidemiology of multidrug-resistant tuberculosis, New York City, 1995-1997.
2002 Nov
[Incidence of adverse reactions to chemotherapy and their types in adolescents with tuberculosis].
2003
[14C]serine from phosphatidylserine labels ceramide and sphingomyelin in L929 cells: evidence for a new metabolic relationship between glycerophospholipids and sphingolipids.
2003 Feb 1
Effects of D-cycloserine on negative symptoms in schizophrenia.
2004 Dec 1
Psychiatric issues in the management of patients with multidrug-resistant tuberculosis.
2004 Jun
Effects of NMDA receptor-related agonists on learning and memory impairment in olfactory bulbectomized mice.
2004 Mar
Model structures of the N-methyl-D-aspartate receptor subunit NR1 explain the molecular recognition of agonist and antagonist ligands.
2004 Mar
Multidrug resistant miliary tuberculosis and Pott's disease in an immunocompetent patient.
2004 Oct
Structural evidence that alanine racemase from a D-cycloserine-producing microorganism exhibits resistance to its own product.
2004 Oct 29
Self-protection mechanism in D-cycloserine-producing Streptomyces lavendulae. Gene cloning, characterization, and kinetics of its alanine racemase and D-alanyl-D-alanine ligase, which are target enzymes of D-cycloserine.
2004 Oct 29
Differential neuroprotective effects of the NMDA receptor-associated glycine site partial agonists 1-aminocyclopropanecarboxylic acid (ACPC) and D-cycloserine in lithium-pilocarpine status epilepticus.
2004 Sep
Facilitation of fear extinction by D-cycloserine: theoretical and clinical implications.
2004 Sep-Oct
Patents

Sample Use Guides

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
Multidrug resistant Mycobacterium tuberculosis isolates were incubated with 20 uL of cycloserine. 5 different cycloserine concentrations (8, 16, 32, 64, and > 64 ug/mL).
Name Type Language
CYCLOSERINE
HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
(+)-4-AMINO-3-ISOXAZOLIDINONE
Systematic Name English
CYCLOSERINE [WHO-IP]
Common Name English
SEROMYCIN
Brand Name English
CYCLOSERINE [USP MONOGRAPH]
Common Name English
CYCLOSERINE [MI]
Common Name English
CYCLOSERINUM [WHO-IP LATIN]
Common Name English
D-CYCLOSERINE
Common Name English
CYCLOSERINE [USP]
Common Name English
ORIENTOMYCIN
Common Name English
3-ISOXAZOLIDINONE, 4-AMINO-, (R)-
Systematic Name English
NSC-76029
Code English
CYCLOSERINE [ORANGE BOOK]
Common Name English
CYCLOSERINE [INN]
Common Name English
CYCLOSERINE [VANDF]
Common Name English
CYCLOSERINE [WHO-DD]
Common Name English
NSC-154851
Code English
CYCLOSERINE [JAN]
Common Name English
CYCLOSERINE [HSDB]
Common Name English
CYCLOSERINE [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ04AB01
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
WHO-ATC J04AB01
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
LIVERTOX 249
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
NCI_THESAURUS C280
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.2.4
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
Code System Code Type Description
MESH
D003523
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
INN
577
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
FDA UNII
95IK5KI84Z
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
LACTMED
Cycloserine
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
HSDB
3218
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
MERCK INDEX
M4019
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY Merck Index
WHO INTERNATIONAL PHARMACOPEIA
CYCLOSERINE
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY Description: A white or pale yellow, crystalline, powder.Solubility: Freely soluble in water; slightly soluble in methanol R and propylene glycol R; very slightly soluble in ethanol (~750 g/l)TS; practically insoluble in dichloromethane R.Category: Antibacterial drug; antituberculosis drug.Storage: Cycloserine should be kept in a tightly closed container.Additional information: Cycloserine is slightly hygroscopic and degrades upon exposure to a humid atmosphere, decompositionbeing faster at higher temperatures.
NCI_THESAURUS
C47466
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
EPA CompTox
68-41-7
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
DRUG BANK
DB00260
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
ChEMBL
CHEMBL771
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
EVMPD
SUB06863MIG
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
DRUG CENTRAL
759
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-688-4
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
PUBCHEM
6234
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
RXCUI
3007
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
CYCLOSERINE
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
CAS
68-41-7
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY
USP_CATALOG
1158005
Created by admin on Fri Jun 25 20:53:29 UTC 2021 , Edited by admin on Fri Jun 25 20:53:29 UTC 2021
PRIMARY USP-RS