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

Details

Stereochemistry ABSOLUTE
Molecular Formula C3H6N2O2
Molecular Weight 102.0919
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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

1964
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
Cycloserine: antituberculous activity in vitro and in the experimental animal.
1956 Apr
Spectrum of drugs against atypical mycobacteria: how valid is the current practice of drug susceptibility testing and the choice of drugs?
1992 Dec
[Effect of glutoxim in the combination with antitubercular agents of the second choice on the growth of drug resistant Mycobacteria tuberculosis in the cultured murine lung tissue].
2002
D-cycloserine for Alzheimer's disease.
2002
De novo-synthesized ceramide is involved in cannabinoid-induced apoptosis.
2002 Apr 1
Pilot-controlled trial of D-cycloserine for the treatment of post-traumatic stress disorder.
2002 Dec
Homer 1a gene expression modulation by antipsychotic drugs: involvement of the glutamate metabotropic system and effects of D-cycloserine.
2002 Dec
Ceramide signaling in fenretinide-induced endothelial cell apoptosis.
2002 Dec 20
A case series of D-cycloserine added to donepezil in the treatment of Alzheimer's disease.
2002 Fall
Evidence for de novo sphingolipid biosynthesis in Toxoplasma gondii.
2002 Jun
A pathway-specific cell based screening system to detect bacterial cell wall inhibitors.
2002 Mar
Facilitation of conditioned fear extinction by systemic administration or intra-amygdala infusions of D-cycloserine as assessed with fear-potentiated startle in rats.
2002 Mar 15
Increased phasic activity of dopaminergic neurones in the rat ventral tegmental area following pharmacologically elevated levels of endogenous kynurenic acid.
2002 May
Molecular epidemiology of multidrug-resistant tuberculosis, New York City, 1995-1997.
2002 Nov
Molecular epidemiology of tuberculosis in a sentinel surveillance population.
2002 Nov
Effects of D-cycloserine on extinction of conditioned freezing.
2003 Apr
Subunit interaction of monomeric alanine racemases from four Shigella species in catalytic reaction.
2003 Apr 25
Multidrug-resistant tuberculosis in HIV-negative patients, Buenos Aires, Argentina.
2003 Aug
D-cycloserine-Naloxone interactions in opioid-dependent humans under a novel-response naloxone discrimination procedure.
2003 Aug
Substrate reduction intervention by L-cycloserine in twitcher mice (globoid cell leukodystrophy) on a B6;CAST/Ei background.
2003 Aug 14
Cycloserine and threo-dihydrosphingosine inhibit TNF-alpha-induced cytotoxicity: evidence for the importance of de novo ceramide synthesis in TNF-alpha signaling.
2003 Dec 7
N(2)-substituted D,L-cycloserine derivatives: synthesis and evaluation as alanine racemase inhibitors.
2003 Feb
Activities of moxifloxacin alone and in combination with other antimicrobial agents against multidrug-resistant Mycobacterium tuberculosis infection in BALB/c mice.
2003 Jan
Effects of antibiotics that inhibit the bacterial peptidoglycan synthesis pathway on moss chloroplast division.
2003 Jul
D-cycloserine for the treatment of ataxia in spinocerebellar degeneration.
2003 Jun 15
Comparative roles of levofloxacin and ofloxacin in the treatment of multidrug-resistant tuberculosis: preliminary results of a retrospective study from Hong Kong.
2003 Oct
Genome-wide transcriptional profiling of the response of Staphylococcus aureus to cell-wall-active antibiotics reveals a cell-wall-stress stimulon.
2003 Oct
Molecular cloning of a D-cycloserine resistance gene from D-cycloserine-producing Streptomyces garyphalus.
2003 Sep
Pharmacokinetics and relative bioavailability of clofazimine in relation to food, orange juice and antacid.
2004
Pharmacological treatments of cerebellar ataxia.
2004
Six-month therapy with aerosolized interferon-gamma for refractory multidrug-resistant pulmonary tuberculosis.
2004 Apr
Glycine and D-cycloserine attenuate vacuous chewing movements in a rat model of tardive dyskinesia.
2004 Apr 9
Pharmacy data for tuberculosis surveillance and assessment of patient management.
2004 Aug
Pharmacotherapy for performance anxiety disorders: occasionally useful but typically contraindicated.
2004 Aug
Consolidation of human motor cortical neuroplasticity by D-cycloserine.
2004 Aug
Effects of D-cycloserine on negative symptoms in schizophrenia.
2004 Dec 1
A microplate indicator-based method for determining the susceptibility of multidrug-resistant Mycobacterium tuberculosis to antimicrobial agents.
2004 Feb
Comparative effects of glycine and D-cycloserine on persistent negative symptoms in schizophrenia: a retrospective analysis.
2004 Feb 1
Reactions of serine palmitoyltransferase with serine and molecular mechanisms of the actions of serine derivatives as inhibitors.
2004 Feb 3
Responsiveness to brightness change in male and female rats following treatment with the partial agonist of the N-methyl-D-aspartate receptor, D-cycloserine.
2004 Jul 9
Surveillance of Mycobacterium tuberculosis susceptibility to second-line drugs in Hong Kong, 1995-2002, after the implementation of DOTS-plus.
2004 Jun
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
Cognitive enhancers as adjuncts to psychotherapy: use of D-cycloserine in phobic individuals to facilitate extinction of fear.
2004 Nov
A pilot study of D-cycloserine in subjects with autistic disorder.
2004 Nov
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
A six-month, placebo-controlled trial of D-cycloserine co-administered with conventional antipsychotics in schizophrenia patients.
2005 Apr
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:12:34 GMT 2023
Edited
by admin
on Fri Dec 15 15:12:34 GMT 2023
Record UNII
95IK5KI84Z
Record Status Validated (UNII)
Record Version
  • Download
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
ORIENTOMYCIN
Common Name English
3-ISOXAZOLIDINONE, 4-AMINO-, (R)-
Systematic Name English
CYCLOSERINE [USP IMPURITY]
Common 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 Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
WHO-ATC J04AB01
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
LIVERTOX NBK547876
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
NCI_THESAURUS C280
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 6.2.4
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
Code System Code Type Description
MESH
D003523
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
INN
577
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
FDA UNII
95IK5KI84Z
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
LACTMED
Cycloserine
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
NSC
154851
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
HSDB
3218
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
NSC
76029
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
MERCK INDEX
m4019
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY Merck Index
WHO INTERNATIONAL PHARMACOPEIA
CYCLOSERINE
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
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 Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID8022870
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
DRUG BANK
DB00260
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
CHEBI
23503
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
ChEMBL
CHEMBL771
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
EVMPD
SUB06863MIG
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
RS_ITEM_NUM
1158005
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PRIMARY
CHEBI
40009
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PRIMARY
CHEBI
75929
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PRIMARY
DRUG CENTRAL
759
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PRIMARY
ECHA (EC/EINECS)
200-688-4
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
PUBCHEM
6234
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
DAILYMED
95IK5KI84Z
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
RXCUI
3007
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
CYCLOSERINE
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
SMS_ID
100000083776
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
CAS
68-41-7
Created by admin on Fri Dec 15 15:12:34 GMT 2023 , Edited by admin on Fri Dec 15 15:12:34 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
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IMPURITY -> PARENT
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC