Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00158)
Name
Cycloserine
Synonyms    Click to Show/Hide the Synonyms of This API
D-cycloserine; cycloserine; 68-41-7; Seromycin; orientomycin; Oxamycin; Cyclo-D-serine; Cyclorin; D-4-amino-3-isoxazolidinone; Cicloserina; Farmiserina; Miroseryn; Tisomycin; Wasserina; Closina; D-4-amino-3-isoxazolidone; alpha-Cycloserine; (+)-4-Amino-3-isoxazolidinone; Cycloserinum; Miroserina; Tebemicina; Novoserin; (R)-4-AMINOISOXAZOLIDIN-3-ONE; (+)-Cycloserine; Oxamicina; (4R)-4-amino-1,2-oxazolidin-3-one; D-(+)-Cycloserine; (4R)-4-aminoisoxazolidin-3-one; Cycloserin; Micoserina; (R)-4-AMINO-ISOXAZOLIDIN-3-ONE; D-Oxamycin; RO-1-9213; E-733-A; 3-Isoxazolidinone, 4-amino-, (4R)-; D-4-Amino-3-isossazolidone; 3-Isoxazolidinone, 4-amino-, (R)-; (R)-4-Amino-3-isoxazolidinone; HSDB 3218; D-Oxamicina; 3-Isoxazolidinone, 4-amino-, d-; UNII-95IK5KI84Z; (R)-(+)-4-Amino-3-isoxazolidinone; I-1431; 3-Isoxazolidinone, 4-amino-, (+)-; NSC 154851; CHEBI:40009; AI3-50153; D-Cycloserine, synthetic; MFCD00005353; CHEMBL771; SC-49088; 95IK5KI84Z; CAS-68-41-7; NCGC00016306-01; D-Cycloserine, 98%; Oxamicina [Italian]; Cicloserina [Italian]; DSSTox_CID_2870; 3-Isoxazolidinone, 4-amino-, (+)- (8CI); DSSTox_RID_76766; DSSTox_GSID_22870; Cycloserinum [INN-Latin]; Cicloserina [INN-Spanish]; Cycloserine, D-; Closerin; .alpha.-Cycloserine; (R)-Cycloserine; Seromycin (TN); SMR000058313; D-4-Amino-3-isossazolidone [Italian]; R-(+)-Cycloserine; (4R)-4-Amino-3-isoxazolidinone; CYCLOSERINE (D); SR-01000075432; DRG-0195; (R)-(+)-Cycloserine; EINECS 200-688-4; D-amino-3-isoxazolidinone; BRN 0080798; (R)-4-Amino-3-isoxazolidone; NSC-76029; Serine, cyclo-; NSC-154851; 3-Isoxazolidinone, 4-amino-, D; R(+)-4-Amino-3-isoxazolidinone; Cycloserine [USP:INN:BAN:JAN]; 3-Isoxazolidinone, 4-amino-, (R); Cycloserine, D(+); PubChem5763; D-Cycloserine, powder; Spectrum_000860; Prestwick0_001089; Prestwick1_001089; Prestwick2_001089; Prestwick3_001089; Spectrum2_000084; Spectrum3_000371; Spectrum4_000305; Spectrum5_000797; Lopac-C-1159; Lopac-C-3909; Lopac-C-7005; 3-Isoxazolidinone, 4-amino-, (4R)- (9CI); C 3909; C-9390; C-9400; Lopac0_000252; SCHEMBL34322; BSPBio_001138; BSPBio_002121; KBioGR_000890; KBioSS_001340; 4-27-00-05549 (Beilstein Handbook Reference); MLS000758215; MLS001423962; MLS002548887; BIDD:GT0707; D-Cycloserine synth. BP 88; DivK1c_000098; SPECTRUM1500215; SPBio_000008; SPBio_003029; BPBio1_001252; FA6C7F8B-D080-4EA3-978F-1ECFB5A29D09; GTPL9489; Cycloserine (JP17/USP/INN); 4-Amino-3-isoxazolidinone, D-; DTXSID8022870; HMS500E20; KBio1_000098; KBio2_001340; KBio2_003908; KBio2_006476; KBio3_001341; NINDS_000098; HMS1571I20; HMS1920C06; HMS2051C15; HMS2091I14; HMS2098I20; HMS2232F03; HMS3259L19; HMS3260D06; HMS3715I14; Pharmakon1600-01500215; (R)-3-Isoxazolidinone, 4-amino-; 4-Amino-3-isoxazolidinone, (R)-; ACT04767; HY-B0030; Tox21_110361; Tox21_500252; BDBM50038178; BDBM50103516; CCG-39705; D-Cycloserine, >=96.0% (NT); LMPK14000007; NSC756712; ZINC34676245; 4-Isoxazolidinamine, 3-oxo-, (D)-; AKOS015994626; Tox21_110361_1; AC-4721; DB00260; HS-0079; LP00252; MCULE-4212827696; NC00050; NC00676; NSC-756712; SDCCGSBI-0050240.P005; IDI1_000098; SMP1_000167; NCGC00015213-01; NCGC00015213-02; NCGC00015213-03; NCGC00016306-02; NCGC00016306-03; NCGC00016306-04; NCGC00016306-05; NCGC00016306-07; NCGC00016306-08; NCGC00016306-17; NCGC00093713-01; NCGC00093713-02; NCGC00260937-01; BR-26256; CAS-339-72-0; ST075697; SBI-0050240.P004; AB0007232; AB00443920; EU-0100252; (4R)-4-amino-2,4,5-trihydroisoxazol-3-one; C08057; D00877; AB00443920_09; AB00443920_10; 005C353; 101039-EP2295402A2; 101039-EP2301544A1; Q418508; SR-01000759389; SR-01000075432-1; SR-01000075432-2; SR-01000075432-5; SR-01000075432-9; SR-01000759389-4; SR-01000075432-10; F2173-1228; Z1522567171; Cycloserine, United States Pharmacopeia (USP) Reference Standard; Cycloserine, Pharmaceutical Secondary Standard; Certified Reference Material
Clinical Status
Approved
Disease Indication Dementia ICD-11: 6D8Z [1]
PubChem CID
6234
Formula
C3H6N2O2
Canonical SMILES
C1[C@H](C(=O)NO1)N
InChI
1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
InChIKey
DYDCUQKUCUHJBH-UWTATZPHSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=6234"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 102.09 Topological Polar Surface Area 64.4
XlogP -1.5 Complexity 92.9
Heavy Atom Count 7 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Cycloserine 250 mg capsule Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Methylparaben; Sodium lauryl sulfate; Butylparaben; D&c yellow no. 10; Benzyl alcohol; Fd&c blue no. 1; Fd&c yellow no. 6; Propylparaben; Sodium propionate; Ferrosoferric oxide; Titanium dioxide; Fd&c red no. 3; Gelatin
                   Dosage Form Oral Capsule
                   Company Purdue GMP Center LLC dba The Chao Center
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [3]
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [4]
Butylparaben DIG Info Estrogen receptor alpha (IC50 = 1420 nM) [5]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [6]
Propyl 4-hydroxybenzoate DIG Info Estrogen receptor alpha (IC50 = 11 uM) [6]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [6]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
D&c yellow no. 10; Fd&c blue no. 1; Fd&c yellow no. 6; Talc; Titanium dioxide; Fd&c red no. 3; Gelatin
                   Dosage Form Oral Capsule
                   Company RemedyRepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [6]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [6]
References
1 FDA label for approved cycloserine from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15; 21(6):1564-9.
4 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.
5 Disconnecting the Estrogen Receptor Binding Properties and Antimicrobial Properties of Parabens through 3,5-Substitution. ACS Med Chem Lett. 2017 Dec 15; 9(1):51-55.
6 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.

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