Details of the Drug

General Information of Drug (ID: DMT1I52)

• Drug Name: Cycloserine
• Synonyms: D-cycloserine; cycloserine; 68-41-7; Seromycin; orientomycin; Oxamycin; Cyclorin; Cyclo-D-serine; Wasserina; Farmiserina; Tisomycin; Cicloserina; Miroseryn; Closina; D-4-amino-3-isoxazolidinone; (R)-4-AMINOISOXAZOLIDIN-3-ONE; alpha-Cycloserine; (+)-4-Amino-3-isoxazolidinone; Miroserina; Cycloserinum; D-4-amino-3-isoxazolidone; Oxamicina; (4R)-4-aminoisoxazolidin-3-one; PA 94; (+)-Cycloserine; (4R)-4-amino-1,2-oxazolidin-3-one; Oxamicina [Italian]; Cycloserin; Micoserina; Cicloserina [Italian]; PA-94; Tebemicina; Novoserin; D-Oxamycin; Cicloserina; Closerin; Orientomycin; C 3909; Alpha-Cycloserine; C-9390; C-9400; Cicloserina [INN-Spanish]; Cycloserinum [INN-Latin]; D-CS; DRG-0195; I-1431; K-300; SC-49088; Seromycin (TN); Cycloserine [INN:BAN:JAN]; E-733-A; RO-1-9213; Cycloserine (JP15/USP/INN); D-amino-3-isoxazolidinone; D-(+)-Cycloserine; D-4-Amino-3-isossazolidone; D-4-Amino-3-isossazolidone [Italian]; FA6C7F8B-D080-4EA3-978F-1ECFB5A29D09; R-(+)-Cycloserine; R-4-Amino-3-isoxazolidinone; R(+)-4-Amino-3-isoxazolidinone; (4R)-4-Amino-3-isoxazolidinone; (R)-(+)-4-Amino-3-isoxazolidinone; (R)-(+)-Cycloserine; (R)-4-AMINO-ISOXAZOLIDIN-3-ONE; (R)-4-Amino-3-isoxazolidinone; (R)-4-Amino-3-isoxazolidone; (R)-Cycloserine; 3-Isoxazolidinone, 4-amino-, (+)-(8CI); 3-Isoxazolidinone, 4-amino-, (4R)-(9CI); 3-Isoxazolidinone, 4-amino-, (R); 3-Isoxazolidinone, 4-amino-, D; (R)-4-Amino-Isoxazolidin-3-One

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Approved	[1]
Pulmonary tuberculosis	1B10.Z	Approved	[2]
Tuberculosis	1B10-1B14	Approved	[3]
Obsessive compulsive disorder	6B20	Phase 2	[1]

• Therapeutic Class: Antiinfective Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 102.09
  Logarithm of the Partition Coefficient (xlogp); -1.5
  Rotatable Bond Count (rotbonds); 0
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 3
• ADMET Property:
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [4]
  Bioavailability: 80% of drug becomes completely available to its intended biological destination(s) [5]
  Elimination: 65% of drug is excreted from urine in the unchanged form [4]
  Half-life: The concentration or amount of drug in body reduced by one-half in 10 hours [6]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 163.57559 micromolar/kg/day [7]
  Water Solubility: The ability of drug to dissolve in water is measured as 100 mg/mL [4]
• Chemical Identifiers:
  Formula: C3H6N2O2
  IUPAC Name: (4R)-4-amino-1,2-oxazolidin-3-one
  Canonical SMILES: C1[C@H](C(=O)NO1)N
  InChI: InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
  InChIKey: DYDCUQKUCUHJBH-UWTATZPHSA-N
• Cross-matching ID:
  PubChem CID: 6234
  ChEBI ID: CHEBI:40009
  CAS Number: 68-41-7
  DrugBank ID: DB00260
  TTD ID: D02WFK
  VARIDT ID: DR00197
  ACDINA ID: D00158
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Glutamate receptor ionotropic NMDA 1 (NMDAR1)	TTLD29N	NMDZ1_HUMAN	Inhibitor	[8]
Mycobacterium Biosynthetic alanine racemase (MycB alr)	TT6TMZU	ALR_MYCSM	Inhibitor	[8]
Mycobacterium D-alanine-D-alanine ligase A (MycB ddl)	TTCS3P1	DDL_MYCTU	Inhibitor	[9]
N-methyl-D-aspartate receptor (NMDAR)	TT9IK2Z	NOUNIPROTAC	Agonist	[10]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Proton-coupled amino acid transporter 2 (SLC36A2)	DTAOPTV	S36A2_HUMAN	Substrate	[11]
Proton-coupled amino acid transporter 1 (SLC36A1)	DT48WEM	S36A1_HUMAN	Substrate	[12]

Molecular Expression Atlas of This Drug

• The Studied Disease: Bacterial infection
• ICD Disease Classification: 1A00-1C4Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Proton-coupled amino acid transporter 1 (SLC36A1)	DTP	PAT1	3.58E-01	7.00E-02	2.27E-01

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Cycloserine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Ethanol	DMDRQZU	Major	Additive CNS depression effects by the combination of Cycloserine and Ethanol.	Cystitis [GC00]	[13]
Polyethylene glycol	DM4I1JP	Moderate	Increased risk of lowers seizure threshold by the combination of Cycloserine and Polyethylene glycol.	Irritable bowel syndrome [DD91]	[14]
Bupropion	DM5PCS7	Major	Increased risk of lowers seizure threshold by the combination of Cycloserine and Bupropion.	Nicotine use disorder [6C4A]	[15]
Lindane	DMB8CNL	Moderate	Increased risk of lowers seizure threshold by the combination of Cycloserine and Lindane.	Pediculosis [1G00]	[16]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent
Butylparaben	E00142	7184	Antimicrobial preservative
FD&C blue no. 1	E00263	19700	Colorant
methylparaben	E00149	7456	Antimicrobial preservative
Propyl 4-hydroxybenzoate	E00141	7175	Antimicrobial preservative
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF	E00255	17730	Colorant
FD&C red no. 3	E00629	Not Available	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Sodium propionate	E00445	2723816	Antimicrobial preservative
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Cycloserine 250 mg capsule	250 mg	Oral Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92.
• [2] Cycloserine FDA Label
• [3] Novel agents in the management of Mycobacterium tuberculosis disease. Curr Med Chem. 2007;14(18):2000-8.
• [4] BDDCS applied to over 900 drugs
• [5] Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
• [6] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [7] Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
• [8] How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
• [9] Self-protection mechanism in D-cycloserine-producing Streptomyces lavendulae. Gene cloning, characterization, and kinetics of its alanine racemase ... J Biol Chem. 2004 Oct 29;279(44):46143-52.
• [10] How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
• [11] Substrate specificity and functional characterisation of the H+/amino acid transporter rat PAT2 (Slc36a2). Br J Pharmacol. 2005 Jan;144(1):28-41.
• [12] Indirect regulation of the intestinal H+-coupled amino acid transporter hPAT1 (SLC36A1). J Cell Physiol. 2005 Aug;204(2):604-13.
• [13] Cerner Multum, Inc. "UK Summary of Product Characteristics.".
• [14] Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
• [15] Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA.
• [16] Matsuoka LY "Convulsions following application of gamma benzene hexachloride." J Am Acad Dermatol 5 (1981): 98-9. [PMID: 6168673]