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Pentamidine

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Name

Pentamidine

EINECS 202-841-0
CAS No. 100-33-4 Density 1.2 g/cm3
PSA 118.20000 LogP 4.48290
Solubility N/A Melting Point 186 °C (dec.)
Formula C19H24N4O2 Boiling Point 539.4 °C at 760 mmHg
Molecular Weight 466.558 Flash Point 280 °C
Transport Information N/A Appearance Crystalline Solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 100-33-4 (Pentamidine) Hazard Symbols N/A
Synonyms

Benzamidine,4,4'-(pentamethylenedioxy)di- (6CI,7CI,8CI);4,4'-(Pentamethylenedioxy)dibenzamidine;4,4'-Diamidino-a,w-diphenoxypentane;MP 601205;NSC 9921;Pentamidine;p,p'-(Pentamethylenedioxy)dibenzamidine;

Article Data 9

Pentamidine Specification

The 4,4'-Diamidinodiphenoxypentane is an organic compound with the formula C19H24N4O2. The IUPAC name of this chemical is 4-[5-(4-carbamimidoylphenoxy)pentoxy]benzenecarboximidamide. With the CAS registry number 100-33-4, it is also named as 1,5-bis(4-amidinophenoxy)pentane. The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is a crystalline solid, which has been widely used as a drug to treat protozoal diseases, such as malaria, amoebic dysentery and trypanosomiasis. It has also been shown to be effective for both prophylaxis of pneumocystic carinii pneumonia (PCC).

Physical properties about 4,4'-Diamidinodiphenoxypentane are: (1)ACD/LogP: 2.47; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -0.53; (4)ACD/LogD (pH 7.4): -0.53; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 6; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 49.66 Å2; (13)Index of Refraction: 1.593; (14)Molar Refractivity: 95.45 cm3; (15)Molar Volume: 281.4 cm3; (16)Polarizability: 37.83×10-24cm3; (17)Surface Tension: 49.1 dyne/cm; (18)Density: 1.2 g/cm3; (19)Flash Point: 280 °C; (20)Enthalpy of Vaporization: 81.68 kJ/mol; (21)Boiling Point: 539.4 °C at 760 mmHg; (22)Vapour Pressure: 1.06E-11 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O(c1ccc(cc1)C(=[N@H])N)CCCCCOc2ccc(C(=[N@H])N)cc2
(2)InChI: InChI=1/C19H24N4O2/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23)
(3)InChIKey: XDRYMKDFEDOLFX-UHFFFAOYAC
(4)Std. InChI: InChI=1S/C19H24N4O2/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23)
(5)Std. InChIKey: XDRYMKDFEDOLFX-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 subcutaneous 100mg/kg (100mg/kg)   Bulletin de la Societe Chimique de France. Vol. -, Pg. 376, 1968.
man TDLo intramuscular 28mg/kg/1W-I (28mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Archives of Internal Medicine. Vol. 145, Pg. 2247, 1985.
man TDLo parenteral 4mg/kg/3D (4mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Lancet. Vol. 246, Pg. 338, 1944.
mouse LD50 intraperitoneal 50mg/kg (50mg/kg)   Journal of Medicinal Chemistry. Vol. 18, Pg. 794, 1975.
women TDLo parenteral 4mg/kg (4mg/kg) ENDOCRINE: HYPOGLYCEMIA Annals of Internal Medicine. Vol. 99, Pg. 128, 1983.

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