Streptovaricin
Title: Streptovaricin
CAS Registry Number: 1404-74-6
Additional Names: Streptovarycin
Literature References: A complex of ansamycin antibiotics consisting of streptovaricins A, B, C, D, E, F, G, J and K of which streptovaricin C is the major component. Isolation from Streptomyces spectabilis: Siminoff et al., Am. Rev. Tuberc. Pulm. Dis. 75, 576 (1957); Whitfield et al., ibid. 584; and resolution of components: Dietz et al., US 3116202 (1963 to Upjohn). Characterization of complex: Rinehart et al., Chem. Commun. 1974, 861. Preliminary structural studies: Rinehart et al., J. Am. Chem. Soc. 88, 3149, 3150 (1966); 90, 6241 (1968); Rinehart et al., ibid. 93, 6273 (1971). Revised structure of streptovaricin C: Sasaki et al., J. Antibiot. 25 68 (1972); Rinehart, Antosz, ibid. 71. Activity studies: Quintrell, McAuslan, J. Virol. 6, 485 (1970); Tan, McAuslan, Biochem. Biophys. Res. Commun. 42, 230 (1971); Carter et al., Nature New Biol. 232, 212, 214 (1971). Biosynthetic study: P. V. Deshmukh et al., J. Am. Chem. Soc. 98, 870 (1976). 13C-NMR studies: K. B. Kakinuma et al., J. Org. Chem. 41, 1358 (1976). Synthesis of a key intermediate for the total synthesis of streptovaricin A: P. A. McCarthy, Tetrahedron Lett. 23, 4199 (1982). Synthesis of the naphthalene core of streptovaricin D: B. M. Trost, W. H. Pearson, ibid. 24, 269 (1983). Review of the chemistry of streptovaricins: K. L. Rinehart et al., Fortschr. Chem. Org. Naturst. 33, 231-307 (1976).
Properties: The complex yields yellow crystals from ethyl acetate + hexane. Neutral or weakly acidic substance which hydrolyzes on treatment with dil alkali. Stable at room temp for 3-4 days at pH 2.0-6.0. Gradually loses its antibiotic activity while standing at room temp for 2-4 days at pH 7.8.
 
Derivative Type: Streptovaricin A
CAS Registry Number: 23344-16-3
Molecular Formula: C42H53NO16
Molecular Weight: 827.87
Percent Composition: C 60.93%, H 6.45%, N 1.69%, O 30.92%
Properties: mp 194-196°. [a]D in chloroform +61°. uv max (95% ethanol): 245, 260, 320, 430 nm (E1%1cm 418.9, 352.1, 139.8, 136.2).
Melting point: mp 194-196°
Optical Rotation: [a]D in chloroform +61°
Absorption maximum: uv max (95% ethanol): 245, 260, 320, 430 nm (E1%1cm 418.9, 352.1, 139.8, 136.2)
 
Derivative Type: Streptovaricin B
CAS Registry Number: 11031-82-6
Molecular Formula: C42H53NO15
Molecular Weight: 811.87
Percent Composition: C 62.13%, H 6.58%, N 1.73%, O 29.56%
Properties: mp 185-187°. [a]D in chloroform +576° (Dietz, +454°). uv max (95% ethanol): 245, 266, 320, 432 nm (E1%1cm 408.3, 338.5, 140.1, 109.7).
Melting point: mp 185-187°
Optical Rotation: [a]D in chloroform +576° (Dietz, +454°)
Absorption maximum: uv max (95% ethanol): 245, 266, 320, 432 nm (E1%1cm 408.3, 338.5, 140.1, 109.7)
 
Derivative Type: Streptovaricin C
CAS Registry Number: 23344-17-4
Molecular Formula: C40H51NO14
Molecular Weight: 769.83
Percent Composition: C 62.41%, H 6.68%, N 1.82%, O 29.10%
Properties: mp 189-191° (Dietz, 168-171°). [a]D in chloroform +602° (Dietz, +317°). uv max (95% ethanol): 245.5, 260, 320, 430 nm (E1%1cm 443.5, 389.7, 153.1, 121.9). Solubility data: March, Weiss, J. Assoc. Off. Anal. Chem. 50, 457 (1967).
Melting point: mp 189-191° (Dietz, 168-171°)
Optical Rotation: [a]D in chloroform +602° (Dietz, +317°)
Absorption maximum: uv max (95% ethanol): 245.5, 260, 320, 430 nm (E1%1cm 443.5, 389.7, 153.1, 121.9)
 
Derivative Type: Streptovaricin D
CAS Registry Number: 32164-26-4
Molecular Formula: C40H51NO13
Molecular Weight: 753.83
Percent Composition: C 63.73%, H 6.82%, N 1.86%, O 27.59%
Properties: mp 167-170° (Dietz, 115-118°). [a]D in chloroform +436° (Dietz, +102°). uv max (95% ethanol): 246, 264, 320, 433 nm (E1%1cm 431.4, 370.3, 147.7, 105.3).
Melting point: mp 167-170° (Dietz, 115-118°)
Optical Rotation: [a]D in chloroform +436° (Dietz, +102°)
Absorption maximum: uv max (95% ethanol): 246, 264, 320, 433 nm (E1%1cm 431.4, 370.3, 147.7, 105.3)
 
Derivative Type: Streptovaricin E
CAS Registry Number: 35413-63-9
Molecular Formula: C40H49NO14
Molecular Weight: 767.82
Percent Composition: C 62.57%, H 6.43%, N 1.82%, O 29.17%
Properties: mp 102-105°. [a]D24 in chloroform +164°, also reported as +613°. uv max (95% ethanol): 245, 273, 320, 437 nm (E1%1cm 382.2, 346.9, 190.4, 91.9).
Melting point: mp 102-105°
Optical Rotation: [a]D24 in chloroform +164°, also reported as +613°
Absorption maximum: uv max (95% ethanol): 245, 273, 320, 437 nm (E1%1cm 382.2, 346.9, 190.4, 91.9)
 
Derivative Type: Streptovaricin F
CAS Registry Number: 35512-37-9
Molecular Formula: C39H47NO14
Molecular Weight: 753.79
Percent Composition: C 62.14%, H 6.28%, N 1.86%, O 29.72%
 
Derivative Type: Streptovaricin G
CAS Registry Number: 11031-85-9
Molecular Formula: C40H51NO15
Molecular Weight: 785.83
Percent Composition: C 61.14%, H 6.54%, N 1.78%, O 30.54%
Properties: mp 190-192°. [a]D in chloroform +473°.
Melting point: mp 190-192°
Optical Rotation: [a]D in chloroform +473°
 
Derivative Type: Streptovaricin J
CAS Registry Number: 52275-61-3
Molecular Formula: C42H53NO15
Molecular Weight: 811.87
Percent Composition: C 62.13%, H 6.58%, N 1.73%, O 29.56%
Properties: mp 177-180°. [a]D +326° (c = 0.25 in ethanol); +436° (c = 0.094 in chloroform).
Melting point: mp 177-180°
Optical Rotation: [a]D +326° (c = 0.25 in ethanol); +436° (c = 0.094 in chloroform)

Others monographs:
Hypophosphoric AcidNoracymethadolAnisindioneAbscisic Acid
HetastarchThyminePregabalinCoprogen
Mandelic AcidDSIPSenecioTriamterene
TyrosinaseChlorsulfuronCloxotestosteronePranoprofen
©2016 DrugLead US FDA&EMEA