Identification
- Summary
Cycloserine is a broad-spectrum antibiotic used in the treatment of tuberculosis and certain urinary tract infections (UTI).
- Brand Names
- Seromycin
- Generic Name
- Cycloserine
- DrugBank Accession Number
- DB00260
- Background
Antibiotic substance produced by Streptomyces garyphalus.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cycloserine (DB00260)
- Weight
- Average: 102.0919
Monoisotopic: 102.042927446 - Chemical Formula
- C3H6N2O2
- Synonyms
- (+)-4-amino-3-isoxazolidinone
- (+)-cycloserine
- alpha-Cycloserine
- Cicloserina
- cyclo-D-Serine
- Cycloserine
- Cyclosérine
- Cycloserinum
- D-(+)-cycloserine
- D-4-amino-3-isoxazolidinone
- D-4-amino-3-isoxazolidone
- D-Cycloserine
- DCS
- Orientomycin
- α-Cycloserine
- External IDs
- NSC-154851
- NSC-76029
- PA 94
- PA-94
- Ro-1-9213
Pharmacology
- Indication
Used in combination with up to 5 other drugs as a treatment for Mycobacterium avium complex (MAC) and is also used to treat tuberculosis (TB).
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Cycloserine, a broad-spectrum antibiotic, may be bactericidal or bacteriostatic, depending on its concentration at the site of infection and the susceptibility of the organism. Cycloserine works by blocking the formation of these peptidoglycans. By doing this the walls of the bacteria become weak and it results in the death of the bacteria
- Mechanism of action
Cycloserine is an analog of the amino acid D-alanine. It interferes with an early step in bacterial cell wall synthesis in the cytoplasm by competitive inhibition of two enzymes, L-alanine racemase, which forms D-alanine from L-alanine, and D-alanylalanine synthetase, which incorporates D-alanine into the pentapeptide necessary for peptidoglycan formation and bacterial cell wall synthesis.
Target Actions Organism AD-alanine--D-alanine ligase A inhibitorEscherichia coli (strain K12) AAlanine racemase inhibitorMycobacterium avium - Absorption
Rapidly and almost completely absorbed (70 to 90%) from the gastrointestinal tract following oral administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Half-life in patients with normal renal function is 10 hours, and is prolonged in patients with impaired renal function.
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Oral LD50 in mouse is 5290 mg/kg, and in rat is over 5000 mg/kg. Symptoms of a cycloserine overdose include drowsiness, confusion, headache, dizziness, irritability, numbness and tingling, difficulty speaking, paralysis, abnormal behavior, seizures, and unconsciousness.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Cycloserine is combined with Acenocoumarol. Acetophenazine Cycloserine may increase the neurotoxic activities of Acetophenazine. Alimemazine Cycloserine may increase the neurotoxic activities of Alimemazine. Ambroxol The risk or severity of methemoglobinemia can be increased when Cycloserine is combined with Ambroxol. Amisulpride Cycloserine may increase the neurotoxic activities of Amisulpride. Amitriptyline Cycloserine may increase the neurotoxic activities of Amitriptyline. Amitriptylinoxide Cycloserine may increase the neurotoxic activities of Amitriptylinoxide. Amoxapine Cycloserine may increase the neurotoxic activities of Amoxapine. Aripiprazole Cycloserine may increase the neurotoxic activities of Aripiprazole. Aripiprazole lauroxil Cycloserine may increase the neurotoxic activities of Aripiprazole lauroxil. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Do not take with or immediately after a high-fat meal. High-fat meals may reduce the rate of absorption; however, the impact on the extent of absorption is unknown.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Oxamycin (Merck) / Tisomycin (Lilly)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cycloserine Capsule 250 mg/1 Oral Macleods Pharmaceuticals Limited 2019-01-18 Not applicable US 
Seromycin Capsule 250 mg/1 Oral Eli Lilly & Co. Ltd. 1956-09-01 2010-02-08 US Seromycin Cap 250mg Capsule 250 mg / cap Oral Eli Lilly & Co. Ltd. 1994-12-31 1997-08-13 Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cycloserine Capsule 250 mg/1 Oral Dr. Reddy’s Laboratories, Inc. 2023-03-15 Not applicable US Cycloserine Capsule 250 mg/250mg Oral Parsolex Gmp Center, Inc. 2009-03-01 Not applicable US Cycloserine Capsule 250 mg/1 Oral Parsolex Gmp Center, Inc. 2013-09-12 Not applicable US Seromycin Capsule 250 mg/1 Oral Parsolex Gmp Center, Inc. 2009-03-01 Not applicable US Seromycin Capsule 250 mg/1 Oral Remedy Repack 2011-08-02 2011-08-02 US Seromycin Capsule 250 mg/250mg Oral Parsolex Gmp Center, Inc. 2009-03-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Cycloserine Cycloserine (250 mg/1) Capsule Oral Macleods Pharmaceuticals Limited 2019-01-18 Not applicable US
Categories
- ATC Codes
- J04AB01 — Cycloserine
- Drug Categories
- Amino Acids
- Amino Acids, Neutral
- Amino Acids, Peptides, and Proteins
- Anti-Bacterial Agents
- Anti-Infective Agents
- Anti-Infective Agents, Urinary
- Antibiotics, Antitubercular
- Antiinfectives for Systemic Use
- Antimetabolites
- Antimycobacterials
- Drugs for Treatment of Tuberculosis
- Isoxazoles
- Neurotoxic agents
- Noxae
- Oxazoles
- Oxazolidinones
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as isoxazolines. These are compounds containing a five-member unsaturated aliphatic ring, with an oxygen atom adjacent to a nitrogen atoms, and three carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azolines
- Sub Class
- Isoxazolines
- Direct Parent
- Isoxazolines
- Alternative Parents
- Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Monoalkylamines / Hydrocarbon derivatives
- Substituents
- Aliphatic heteromonocyclic compound / Amine / Azacycle / Hydrocarbon derivative / Isoxazoline / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- organooxygen heterocyclic antibiotic, organonitrogen heterocyclic antibiotic, 4-amino-1,2-oxazolidin-3-one (CHEBI:40009) / Non-ribosomal peptide/polyketide hybrids (C08057) / Non-ribosomal peptide/polyketide hybrids (LMPK14000007)
- Affected organisms
- Enteric bacteria and other eubacteria
- Mycobacterium tuberculosis
Chemical Identifiers
- UNII
- 95IK5KI84Z
- CAS number
- 68-41-7
- InChI Key
- DYDCUQKUCUHJBH-UWTATZPHSA-N
- InChI
- InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
- IUPAC Name
- (4R)-4-amino-1,2-oxazolidin-3-one
- SMILES
- N[C@@H]1CONC1=O
References
- Synthesis Reference
Norman P. Jensen, "N-substituted cycloserine compounds, salts thereof, and processes for preparing them." U.S. Patent US3932439, issued December, 1956.
US3932439- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014405
- KEGG Compound
- C08057
- PubChem Compound
- 6234
- PubChem Substance
- 46506865
- ChemSpider
- 5998
- BindingDB
- 50103516
- 3007
- ChEBI
- 40009
- ChEMBL
- CHEMBL771
- ZINC
- ZINC000034676245
- Therapeutic Targets Database
- DAP001468
- PharmGKB
- PA164764600
- PDBe Ligand
- 4AX
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Cycloserine
- PDB Entries
- 1pb9 / 1xql
- MSDS
- Download (73.4 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Basic Science Post Traumatic Stress Disorder (PTSD) 1 4 Completed Treatment Bipolar Disorder (BD) 1 4 Completed Treatment Delusional Disorder / Schizoaffective Disorders / Schizophrenia 1 4 Completed Treatment Obsessive Compulsive Disorder (OCD) 2 4 Completed Treatment Post Traumatic Stress Disorder (PTSD) 1 4 Completed Treatment Schizophrenia 2 4 Completed Treatment Social Anxiety Disorder (SAD) 1 4 Completed Treatment Spinal Cord Injuries 1 4 Recruiting Treatment Multidrug Resistant Tuberculosis 1 4 Terminated Treatment Chronic Prostatitis With Chronic Pelvic Pain Syndrome 1
Pharmacoeconomics
- Manufacturers
- Purdue gmp center llc dba the chao center industrial pharmacy
- Packagers
- Eli Lilly & Co.
- Purdue Pharma LP
- The Chao Center
- Dosage Forms
Form Route Strength Capsule, coated Oral 250 mg Capsule Oral Capsule Oral 250 mg Capsule Oral 250 mg/250mg Capsule Oral 250 mg/1 Capsule Oral 250 mg / cap Tablet 250 mg - Prices
Unit description Cost Unit Seromycin 250 mg capsule 7.53USD each Seromycin 250 mg pulvule 6.0USD each DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 155.5 dec °C PhysProp water solubility Soluble Not Available logP -0.9 Not Available - Predicted Properties
Property Value Source Water Solubility 877.0 mg/mL ALOGPS logP -2.3 ALOGPS logP -2.4 Chemaxon logS 0.93 ALOGPS pKa (Strongest Acidic) 4.21 Chemaxon pKa (Strongest Basic) 8.36 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 64.35 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 21.85 m3·mol-1 Chemaxon Polarizability 8.87 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9909 Blood Brain Barrier + 0.9382 Caco-2 permeable - 0.6038 P-glycoprotein substrate Non-substrate 0.7749 P-glycoprotein inhibitor I Non-inhibitor 0.9306 P-glycoprotein inhibitor II Non-inhibitor 1.0 Renal organic cation transporter Non-inhibitor 0.9522 CYP450 2C9 substrate Non-substrate 0.9244 CYP450 2D6 substrate Non-substrate 0.8168 CYP450 3A4 substrate Non-substrate 0.5966 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9608 Ames test AMES toxic 0.5756 Carcinogenicity Non-carcinogens 0.8944 Biodegradation Not ready biodegradable 0.7842 Rat acute toxicity 1.3414 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9964 hERG inhibition (predictor II) Non-inhibitor 0.9389
Spectra
- Mass Spec (NIST)
- Download (8.89 KB)
- Spectra
Spectrum Spectrum Type Splash Key GC-MS Spectrum - GC-MS (2 TMS) GC-MS splash10-0uy0-5900000000-06bce0b228f324fe49b4 Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - GC-MS GC-MS splash10-0uy0-5900000000-06bce0b228f324fe49b4 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Manganese ion binding
- Specific Function
- Cell wall formation.
- Gene Name
- ddlA
- Uniprot ID
- P0A6J8
- Uniprot Name
- D-alanine--D-alanine ligase A
- Molecular Weight
- 39315.435 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Belanger AE, Porter JC, Hatfull GF: Genetic analysis of peptidoglycan biosynthesis in mycobacteria: characterization of a ddlA mutant of Mycobacterium smegmatis. J Bacteriol. 2000 Dec;182(23):6854-6. [Article]
- Noda M, Kawahara Y, Ichikawa A, Matoba Y, Matsuo H, Lee DG, Kumagai T, Sugiyama M: 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. J Biol Chem. 2004 Oct 29;279(44):46143-52. Epub 2004 Aug 9. [Article]
- McCoy AJ, Maurelli AT: Characterization of Chlamydia MurC-Ddl, a fusion protein exhibiting D-alanyl-D-alanine ligase activity involved in peptidoglycan synthesis and D-cycloserine sensitivity. Mol Microbiol. 2005 Jul;57(1):41-52. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Mycobacterium avium
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Pyridoxal phosphate binding
- Specific Function
- Catalyzes the interconversion of L-alanine and D-alanine.
- Gene Name
- alr
- Uniprot ID
- Q9L888
- Uniprot Name
- Alanine racemase
- Molecular Weight
- 41001.515 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Feng Z, Barletta RG: Roles of Mycobacterium smegmatis D-alanine:D-alanine ligase and D-alanine racemase in the mechanisms of action of and resistance to the peptidoglycan inhibitor D-cycloserine. Antimicrob Agents Chemother. 2003 Jan;47(1):283-91. [Article]
- Fenn TD, Stamper GF, Morollo AA, Ringe D: A side reaction of alanine racemase: transamination of cycloserine. Biochemistry. 2003 May 20;42(19):5775-83. [Article]
- Fenn TD, Holyoak T, Stamper GF, Ringe D: Effect of a Y265F mutant on the transamination-based cycloserine inactivation of alanine racemase. Biochemistry. 2005 Apr 12;44(14):5317-27. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Pyridoxal phosphate binding
- Specific Function
- Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
- Gene Name
- DDC
- Uniprot ID
- P20711
- Uniprot Name
- Aromatic-L-amino-acid decarboxylase
- Molecular Weight
- 53925.815 Da
References
- DENGLER HJ, RAUCHS E, RUMMEL W: [On the inhibition of L-glutamic acid and L-DOPA decarboxylase by D-cycloserine and other isoxazolidones]. Naunyn Schmiedebergs Arch Exp Pathol Pharmakol. 1962;243:366-81. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- L-proline transmembrane transporter activity
- Specific Function
- Involved in a pH-dependent electrogenic neuronal transport and sequestration of small amino acids. Transports glycine and proline. Inhibited by sarcosine (By similarity).
- Gene Name
- SLC36A2
- Uniprot ID
- Q495M3
- Uniprot Name
- Proton-coupled amino acid transporter 2
- Molecular Weight
- 53215.65 Da
References
- Kennedy DJ, Gatfield KM, Winpenny JP, Ganapathy V, Thwaites DT: Substrate specificity and functional characterisation of the H+/amino acid transporter rat PAT2 (Slc36a2). Br J Pharmacol. 2005 Jan;144(1):28-41. [Article]
Drug created at June 13, 2005 13:24 / Updated at April 07, 2023 13:20