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
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
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 |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e1e08327-4b90-463e-bb2a-22438cabcef2Curator's Comment: description was created based on several sources, including ISBN-13: 978-0199337149
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e1e08327-4b90-463e-bb2a-22438cabcef2
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2031 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4919992 |
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Target ID: CHEMBL2030 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4919992 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | SEROMYCIN Approved UseSeromycin 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 Date1964 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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42.92 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25869627 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
643.29 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25869627 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.27 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25869627 |
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
Dose | Population | Adverse 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 |
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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) Sources: Dizziness (below serious, 4 patients) Restlessness (below serious, 7 patients) Sore throat (below serious, 6 patients) Urticaria (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: |
Other AEs: Headache, Vomiting... Other AEs: Headache (below serious, 9 patients) Sources: Vomiting (below serious, 6 patients) Irritability (below serious, 16 patients) Feeling sad (below serious, 5 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
PubMed
Title | Date | PubMed |
---|---|---|
Pathological apoptosis by xanthurenic acid, a tryptophan metabolite: activation of cell caspases but not cytoskeleton breakdown. | 2001 |
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Utility of PCR assays for rapid diagnosis of BCG infection in children. | 2001 Apr |
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Subunit specificity and mechanism of action of NMDA partial agonist D-cycloserine. | 2001 Aug |
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Can cyclosporine go it alone in severe ulcerative colitis? | 2001 Dec |
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Pharmacokinetics of para-aminosalicylic acid granules under four dosing conditions. | 2001 Nov |
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Therapeutic drug monitoring in the treatment of tuberculosis. | 2002 |
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D-cycloserine for Alzheimer's disease. | 2002 |
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Homer 1a gene expression modulation by antipsychotic drugs: involvement of the glutamate metabotropic system and effects of D-cycloserine. | 2002 Dec |
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Impaired visual memory in rats reared in isolation is reversed by D-cycloserine in the adult rat. | 2002 Feb 15 |
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Substrate-reduction therapy enhances the benefits of bone marrow transplantation in young mice with globoid cell leukodystrophy. | 2002 Jan |
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D-Cycloserine added to risperidone in patients with primary negative symptoms of schizophrenia. | 2002 Jul 1 |
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A pathway-specific cell based screening system to detect bacterial cell wall inhibitors. | 2002 Mar |
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Increased phasic activity of dopaminergic neurones in the rat ventral tegmental area following pharmacologically elevated levels of endogenous kynurenic acid. | 2002 May |
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Effects of dietary sphingomyelin on central nervous system myelination in developing rats. | 2003 Apr |
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D-cycloserine-Naloxone interactions in opioid-dependent humans under a novel-response naloxone discrimination procedure. | 2003 Aug |
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In vitro activity of C-8-methoxy fluoroquinolones against mycobacteria when combined with anti-tuberculosis agents. | 2003 Dec |
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Novel antibiotic-resistance markers in pGK12-derived vectors for Borrelia burgdorferi. | 2003 Jan 16 |
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Multidrug-resistant tuberculosis in pregnancy: case report and review of the literature. | 2003 Mar |
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Pharmacokinetics and relative bioavailability of clofazimine in relation to food, orange juice and antacid. | 2004 |
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Glycine and D-cycloserine attenuate vacuous chewing movements in a rat model of tardive dyskinesia. | 2004 Apr 9 |
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Pharmacy data for tuberculosis surveillance and assessment of patient management. | 2004 Aug |
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Pharmacotherapy for performance anxiety disorders: occasionally useful but typically contraindicated. | 2004 Aug |
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A microplate indicator-based method for determining the susceptibility of multidrug-resistant Mycobacterium tuberculosis to antimicrobial agents. | 2004 Feb |
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Comparative effects of glycine and D-cycloserine on persistent negative symptoms in schizophrenia: a retrospective analysis. | 2004 Feb 1 |
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New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method. | 2004 Jan |
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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 |
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Treatment and follow-up of HIV-negative multidrug-resistant tuberculosis patients in an infectious diseases reference hospital, Buenos Aires, Argentina. | 2004 Jun |
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D-cycloserine and the facilitation of extinction of conditioned fear: consequences for reinstatement. | 2004 Jun |
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Self-administered, standardized regimens for multidrug-resistant tuberculosis in South Korea. | 2004 Mar |
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Model structures of the N-methyl-D-aspartate receptor subunit NR1 explain the molecular recognition of agonist and antagonist ligands. | 2004 Mar |
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Ceramide synthesis correlates with the posttranscriptional regulation of the sterol-regulatory element-binding protein. | 2004 May |
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Cognitive enhancers as adjuncts to psychotherapy: use of D-cycloserine in phobic individuals to facilitate extinction of fear. | 2004 Nov |
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A pilot study of D-cycloserine in subjects with autistic disorder. | 2004 Nov |
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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 |
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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
Substance Class |
Chemical
Created
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admin
on
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Record UNII |
95IK5KI84Z
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Record Status |
Validated (UNII)
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WHO-VATC |
QJ04AB01
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WHO-ATC |
J04AB01
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LIVERTOX |
NBK547876
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NCI_THESAURUS |
C280
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WHO-ESSENTIAL MEDICINES LIST |
6.2.4
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D003523
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577
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95IK5KI84Z
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Cycloserine
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154851
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m4019
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CYCLOSERINE
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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. | ||
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C47466
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DTXSID8022870
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DB00260
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23503
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CHEMBL771
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SUB06863MIG
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75929
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759
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200-688-4
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6234
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95IK5KI84Z
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3007
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CYCLOSERINE
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100000083776
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68-41-7
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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