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3485-14-1

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Basic Information
CAS No.: 3485-14-1
Name: Cyclacillin
Molecular Structure:
Molecular Structure of 3485-14-1 (Cyclacillin)
Formula: C15H23 N3 O4 S
Molecular Weight: 341.431
Synonyms: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-(1-aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo- (7CI,8CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, [2S-(2a,5a,6b)]-; (1-Aminocyclohexyl)penicillin; 6-(1-Aminocyclohexanecarboxamido)penicillanicacid; 6-(1-Aminocyclohexylcarboxamido)penicillanic acid;Aminocyclohexylpenicillin; Calthor; Ciclacillin; Ciclacillum; Citosarin;Cyclacillin; Cyclapen; NSC 88789; Penicillin, (aminocyclohexyl)-; Syngacillin;Ultracillin; Vastcillin; Vatracin; Vipicil; Wy 4508; Wyvital
Density: 1.4g/cm3
Melting Point: 182-183° (anhydrate) (Hou, Poole); mp 156-158° (dec) (Alburn et al.)
Boiling Point: 649.6°Cat760mmHg
Flash Point: 346.7°C
Solubility: 32g/L(25 oC)
Safety: Moderately toxic by ingestion and other routes. Human systemic effects by ingestion: dermatitis and diarrhea. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx and NOx.
PSA: 138.03000
LogP: 1.30880
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Chemistry

Molecular Structure of Cyclacillin (CAS NO. 3485-14-1):

EINECS: 222-470-8
IUPAC Name: (2S,5R,6R)-6-[(1-Aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid  
Molecular Formula: C15H23N3O4S
Molecular Weight: 341.425820 g/mol
XLogP3: 1.3
H-Bond Donor: 3
H-Bond Acceptor: 5
Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C3(CCCCC3)N)C(=O)O)C
Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3(CCCCC3)N)C(=O)O)C
InChI: InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1
InChIKey: HGBLNBBNRORJKI-WCABBAIRSA-N
Index of Refraction: 1.631
Molar Refractivity: 86.37 cm3
Molar Volume: 242.3 cm3
Surface Tension: 68.8 dyne/cm
Density: 1.4 g/cm3
Flash Point: 346.7 °C
Enthalpy of Vaporization: 104.45 kJ/mol
Boiling Point: 649.6 °C at 760 mmHg
Vapour Pressure: 1.5E-18 mmHg at 25 °C
Water Solubility: 530.8 mg/L at 25 °C
BRN of Cyclacillin (CAS NO. 3485-14-1): 0938663

Toxicity Data With Reference

1.    

orl-hmn TDLo:210 mg/kg/7D-I:GIT,SKN

     CHTHBK    Chemotherapy. 22 (1976),154.
2.    

orl-rat LD50:5010 mg/kg

     CHTHBK    Chemotherapy. 22 (1976),154.
3.    

ipr-rat LD50:5010 mg/kg

     CHTHBK    Chemotherapy. 22 (1976),154.
4.    

scu-rat LD50:6500 mg/kg

     TAKHAA    Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. 29 (1970),117.
5.    

orl-mus LD50:5010 mg/kg

     CHTHBK    Chemotherapy. 22 (1976),154.
6.    

ipr-mus LD50:3776 mg/kg

     CHTHBK    Chemotherapy. 22 (1976),154.
7.    

scu-mus LD50:7500 mg/kg

     TAKHAA    Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. 29 (1970),117.
8.    

orl-dog LD50:2500 mg/kg

     CHTHBK    Chemotherapy. 22 (1976),154.

Safety Profile

Moderately toxic by ingestion and other routes. Human systemic effects by ingestion: dermatitis and diarrhea. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx and NOx.

Specification

  Cyclacillin with cas registry number of 3485-14-1 is an aminopenicillin antibiotic, also known as (1-Aminocyclohexyl)penicillin ; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((1-aminocyclohexyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))- ; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(1-aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo- (8CI) ; AC 98 ; AC-PC ; Bastcillin ; 6-(1-Aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid ; 6-(1-Aminocyclohexanecarboxamido)penicillanic acid ; 6-(1-Aminocyclohexylcarboxamido)penicillanic acid ; Aminocyclohexyl penicillin ; Aminocyclohexylpenicillin ; Calthor ; Ciclacilina ; Ciclacilina [INN-Spanish] ; Ciclacillin ; Ciclacilline ; Ciclacilline [INN-French] ; Ciclacillinum ; Ciclacillinum [INN-Latin] ; Ciclacillum ; Citosarin ; Cyclapen ; Cyclacillin [USAN] ; Cyclapen-W ; NSC 88789 ; Noblicil ; Orfilina ; Peamezin ; Penicillin, (aminocyclohexyl)- ; Syngacillin ; UNII-72ZJ154X86 ; Ultracillin ; Vastcillin ; Vipicil ; Wy 4508 ; Wypicil ; Wyvital . Cyclacillin is associated with significantly fewer and milder adverse effects than ampicillin at least in children. Ciclacillin has been superseded by newer antibiotics and is no longer in clinical use, at least in the United States.