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Spiramycin, スピラマイシン

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8025-81-8.pngSpiramycin I.svg

ChemSpider 2D Image | [(11E,13E)-6-({5-[(4,5-Dihydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy]-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl}oxy)-10-{[5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy }-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-7-yl]acetaldehyde | C43H74N2O14Spiramycin.png2D chemical structure of 8025-81-8

ThumbChemSpider 2D Image | 033ECH6IFG | C43H74N2O14

Spiramycin

スピラマイシン

CAS: 8025-81-8

Sanofi INNOVATOR

Molecular Formula: C43H74N2O14
Molecular Weight: 843.065 g/mol

[(11E,13E)-6-({5-[(4,5-Dihydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy]-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl}oxy)-10-{[5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy }-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-7-yl]acetaldehyde

2-[(11E,13E)-6-[5-(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde

Leucomycin V, 9-O-[(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]-

033ECH6IFG
24916-50-5 [RN]
Spiramycin I
[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-5-{[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-10-{[(2R,5S,6S)-5-(dimethylamino)-6
  • Provamycin
  • Rovamycin
  • RP 5337
  • Sequamycin
  • IL 5902
  • NSC-64393
  • ATC:J01FA02
  • Use:macrolide antibiotic
  • EINECS:232-429-6
  • LD50:130 mg/kg (M, i.v.); 2900 mg/kg (M, p.o.);
    170 mg/kg (R, i.v.); 3550 mg/kg (R, p.o.);
    5200 mg/kg (dog, p.o.)

2018/7/2 japan approved, UNII: 71ODY0V87H

Solubility

Slightly soluble in water

O’Neil, M.J. (ed.). The Merck Index – An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1621

Soluble in most organic solvents

O’Neil, M.J. (ed.). The Merck Index – An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1621

Spectral Properties

UV max (ethanol): 231nm

O’Neil, M.J. (ed.). The Merck Index – An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1621

Specific optical rotation: -80 deg at 20 deg C/D

O’Neil, M.J. (ed.). The Merck Index – An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1621
スピラマイシン
Spiramycin


スピラマイシン酢酸エステル JP17
Spiramycin Acetate

A macrolide antibiotic produced by Streptomyces ambofaciens. The drug is effective against gram-positive aerobic pathogens, N. gonorrhoeae, and staphylococci. It is used to treat infections caused by bacteria and Toxoplasma gondii.

Spiramycin is a macrolide antimicrobial agent with activity against gram-positive organisms, including Streptococcus pyogenes (group A beta-hemolytic streptococci), S. viridans, Corynebacterium diphtheriae, and methicillin-sensitive Staphylococcus aureus. Spiramycin is a 16-membered ring macrolide. It was discovered in 1952 as a product of Streptomyces ambofaciens. As a preparation for oral administration it has been used since 1955, in 1987 also the parenteral form was introduced into practice. The antibacterial spectrum comprises Gram-positive cocci and rods, Gram-negative cocci and also Legionellae, mycoplasmas, chlamydiae, some types of spirochetes, Toxoplasma gondii and Cryptosporidium species. Enterobacteria, pseudomonads and pathogenic moulds are resistant. Its action is mainly bacteriostatic, on highly sensitive strains it exerts a bactericide action.

Spiramycin is a macrolide antibiotic and antiparasitic It is used to treat toxoplasmosis and various other infections of soft tissues. Although used in Europe, Canada and Mexico,[1] spiramycin is still considered an experimental drug in the United States, but can sometimes be obtained by special permission from the FDA for toxoplasmosis in the first trimester of pregnancy.[2]

Spiramycin has been used in Europe since the year 2000 under the trade name “Rovamycine”, produced by Rhone-Poulenc Rorer and Famar Lyon, France and Eczacıbaşı İlaç, Turkey. It also goes under the name Rovamycine in Canada (distributed by OdanLaboratories), where it is mostly marketed to dentists for mouth infections.

Spiramycin is a 16-membered ring macrolide. It was discovered in 1952 as a product of Streptomyces ambofaciens. As a preparation for oral administration it has been used since 1955, in 1987 also the parenteral form was introduced into practice. The antibiotic action involves inhibition of protein synthesis in the bacterial cell during translocation. Resistance to spiramycin can develop by several mechanisms and its prevalence is to a considerable extent proportional to the frequency of prescription in a given area. The antibacterial spectrum comprises Gram-positive cocci and rods, Gram-negative cocci and also Legionellae, mycoplasmas, chlamydiae, some types of spirochetes, Toxoplasma gondii and Cryptosporidium species. Enterobacteria, pseudomonads and pathogenic moulds are resistant. Its action is mainly bacteriostatic, on highly sensitive strains it exerts a bactericide action. As compared with erythromycin, it is in vitro weight for weight 5 to 20 less effective, an equipotential therapeutic dose is, however, only double. This difference between the effectiveness in vitro and in vivo is explained above all by the great affinity of spiramycin to tissues where it achieves concentrations many times higher than serum levels. An important part is played also by the slow release of the antibiotic from the tissue compartment, the marked action on microbes in sub-inhibition concentrations and the relatively long persisting post-antibiotic effect. Its great advantage is the exceptionally favourable tolerance-gastrointestinal and general. It is available for parenteral and oral administration

Synthesis Path

  • From culture of Streptomyces ambofaciens.

Trade Names

Country Trade Name Vendor Annotation
D Rovamycine Teofarma
Selectomycin Grünenthal
F Bi Missilor Pierre Fabre
Birodogyl Sanofi-Aventis
Missilor Pierre Fabre comb.
Rodogyl Pierre Fabre
Rovamycine Grünenthal
I Rovamicina Sanofi-Aventis
Rovamycina Teofarma
Spiromix Pulitzer

Spiramycin

Title: Spiramycin
CAS Registry Number: 8025-81-8
Manufacturers’ Codes: RP-5337
Trademarks: Selectomycin (Grñenthal); Rovamicina (RPR); Rovamycin (RPR)
Literature References: Antibiotic substance classified in the erythromycin-carbomycin group and produced by Streptomyces ambofaciens from soil of northern France: Cosar et al., C.R. Seances Soc. Biol. Ses Fil. 234, 1498 (1952); Pinnert-Sindico et al.,Antibiot. Annu. 1954-1955, 724; Ninet, Verrier, US 2943023 (1960 to Rhône-Poulenc), see also US 3000785 (1961 to Rhône-Poulenc). Antibacterial activity and toxicity: H. Sous et al., Arzneim.-Forsch. 8, 386 (1958). Separation into 3 components named spiramycin I, II and III: Preud’homme, Charpentier, US 2978380 and US 3011947 (1961 to Rhône-Poulenc). Structure: Kuehne, Benson, J. Am. Chem. Soc. 87, 4660 (1965). Revised structure: Omura et al., ibid. 91, 3401 (1969); Mitscher et al., J. Antibiot. 26,55 (1973). Revised configuration at C-9: Freiberg et al., J. Org. Chem. 39, 2474 (1974). Symposium on pharmacology, antibacterial spectrum, and clinical efficacy: J. Antimicrob. Chemother. 22, Suppl. B, 1-213 (1988).
Properties: Amorphous base, slightly sol in water. [a]D20 -80° (methanol). uv max (ethanol): 231 nm. Sol in most organic solvents. Active on gram-positive bacteria and rickettsiae. Cross resistance between microorganisms resistant to erythromycin and carbomycin. LD50 in rats (mg/kg): 9400 orally; 1000 s.c.; 170 i.v. (Sous).
Optical Rotation: [a]D20 -80° (methanol)
Absorption maximum: uv max (ethanol): 231 nm
Toxicity data: LD50 in rats (mg/kg): 9400 orally; 1000 s.c.; 170 i.v. (Sous)
Derivative Type: Embonate
Trademarks: Spira 200 (RMB)
Derivative Type: Hexanedioate
Additional Names: Spiramycin adipate
Trademarks: Stomamycin (Chassot); Suanovil (Biokema)
Derivative Type: Spiramycin I
CAS Registry Number: 24916-50-5
Additional Names: Foromacidin A
Molecular Formula: C43H74N2O14
Molecular Weight: 843.05
Percent Composition: C 61.26%, H 8.85%, N 3.32%, O 26.57%
Properties: Crystals, mp 134-137°. [a]D20 -96°.
Melting point: mp 134-137°
Optical Rotation: [a]D20 -96°
Derivative Type: Spiramycin I triacetate
Properties: Crystals, mp 140-142°. [a]D20 -92.5°.
Melting point: mp 140-142°
Optical Rotation: [a]D20 -92.5°
Derivative Type: Spiramycin II
CAS Registry Number: 24916-51-6
Additional Names: Foromacidin B
Molecular Formula: C45H76N2O15
Molecular Weight: 885.09
Percent Composition: C 61.07%, H 8.65%, N 3.17%, O 27.11%
Properties: Crystals, mp 130-133°. [a]D20 -86°.
Melting point: mp 130-133°
Optical Rotation: [a]D20 -86°
Derivative Type: Spiramycin II diacetate
Properties: Crystals from cyclohexane, mp 156-160°. [a]D20 -98.4°.
Melting point: mp 156-160°
Optical Rotation: [a]D20 -98.4°
Derivative Type: Spiramycin III
CAS Registry Number: 24916-52-7
Additional Names: Foromacidin C
Molecular Formula: C46H78N2O15
Molecular Weight: 899.12
Percent Composition: C 61.45%, H 8.74%, N 3.12%, O 26.69%
Properties: Crystals, mp 128-131°. [a]D20 -83°.
Melting point: mp 128-131°
Optical Rotation: [a]D20 -83°
Derivative Type: Spiramycin III diacetate
Properties: Crystals from cyclohexane, mp 140-142°. [a]D20 -90.4°.
Melting point: mp 140-142°
Optical Rotation: [a]D20 -90.4°
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial; growth promotant.
Keywords: Antibacterial (Antibiotics); Macrolides.
Spiramycin
Spiramycin I.svg
Clinical data
Synonyms 2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-5-{[(2S,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-10-{[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
Routes of
administration
oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
E number E710 (antibiotics) Edit this at Wikidata
ECHA InfoCard 100.029.476 Edit this at Wikidata
Chemical and physical data
Formula C43H74N2O14
Molar mass 843.053 g/mol
3D model (JSmol)
Solubility in water Insoluble in water; Very soluble in acetonitrile and methanol; Almost completely(>99.5) in ethanol. mg/mL (20 °C)

References

  1. Jump up^ Spiramycin advanced consumer information | Drugs.com
  2. Jump up^ Toxoplasmosis at MayoClinic.com

References

    • Pinnert-Sindico, S. et al.: Antibiot. Annu. (ABANAE) 1954-1955, 724.
    • US 2 943 023 (Rhône-Poulenc; 28.6.1960; F-prior. 30.5.1956).
    • US 2 978 380 (Rhône-Poulenc; 4.4.1961; F-prior. 30.11.1955).
    • US 3 000 785 (Rhône-Poulenc; 19.9.1961; F-prior. 31.7.1953).
    • US 3 011 947 (Rhône-Poulenc; 5.12.1961; F-prior. 30.11.1955).
    • CN 107266512

      CN 107840864

DB06145.png

Spiramycin I)

///////////Spiramycin, スピラマイシン , japan 2018, Provamycin, Rovamycin, RP 5337, Sequamycin, IL 5902, NSC-64393, ATC:J01FA02, Use:macrolide antibiotic, EINECS:232-429-6

 

O=CCC4C(OC2OC(C(OC1OC(C)C(O)C(O)(C)C1)C(N(C)C)C2O)C)C(OC)C(O)CC(=O)OC(C)C\C=C\C=C\C(OC3OC(C)C(N(C)C)CC3)C(C)C4

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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 30 year tenure till date Dec 2017, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 50 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 19 lakh plus views on New Drug Approvals Blog in 216 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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