Colistimethate Sodium

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Also known as: Sodium colistin methanesulfonate, Colistin sulfomethate, Colimycin m, 12705-41-8, Colistinmethanesulfonic acid, Sodium colistimethate

Molecular Formula

C₅₈H₁₀₅N₁₆Na₅O₂₈S₅

Molecular Weight

1749.8 g/mol

InChI Key

IQWHCHZFYPIVRV-UHFFFAOYSA-I

Colistimethate is a broad-spectrum polymyxin antibiotic against most aerobic Gram-negative bacteria except Proteus bacteria. Colistimethate is a mixture of methanesulfonate derivatives of cyclic polypeptides colistin A and B from Bacillus colistinus or B. polymyxa. Colistin functions as a surfactant which penetrates into and disrupts the bacterial cell membrane, thereby resulting in bactericidal effect.

1 2D Structure

Colistimethate Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

pentasodium;[2-[17-(1-hydroxyethyl)-22-[[2-[[3-hydroxy-2-[[2-(6-methyloctanoylamino)-4-(sulfonatomethylamino)butanoyl]amino]butanoyl]amino]-4-(sulfonatomethylamino)butanoyl]amino]-5,8-bis(2-methylpropyl)-3,6,9,12,15,18,23-heptaoxo-11,14-bis[2-(sulfonatomethylamino)ethyl]-1,4,7,10,13,16,19-heptazacyclotricos-2-yl]ethylamino]methanesulfonate

2.1.2 InChI

InChI=1S/C58H110N16O28S5.5Na/c1-9-35(6)12-10-11-13-46(77)65-38(14-20-59-28-103(88,89)90)53(82)74-48(37(8)76)58(87)70-41(17-23-62-31-106(97,98)99)50(79)68-43-19-25-64-57(86)47(36(7)75)73-54(83)42(18-24-63-32-107(100,101)102)67-49(78)39(15-21-60-29-104(91,92)93)69-55(84)44(26-33(2)3)72-56(85)45(27-34(4)5)71-52(81)40(66-51(43)80)16-22-61-30-105(94,95)96;;;;;/h33-45,47-48,59-63,75-76H,9-32H2,1-8H3,(H,64,86)(H,65,77)(H,66,80)(H,67,78)(H,68,79)(H,69,84)(H,70,87)(H,71,81)(H,72,85)(H,73,83)(H,74,82)(H,88,89,90)(H,91,92,93)(H,94,95,96)(H,97,98,99)(H,100,101,102);;;;;/q;5*+1/p-5

2.1.3 InChI Key

IQWHCHZFYPIVRV-UHFFFAOYSA-I

2.1.4 Canonical SMILES

CCC(C)CCCCC(=O)NC(CCNCS(=O)(=O)[O-])C(=O)NC(C(C)O)C(=O)NC(CCNCS(=O)(=O)[O-])C(=O)NC1CCNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCNCS(=O)(=O)[O-])CC(C)C)CC(C)C)CCNCS(=O)(=O)[O-])CCNCS(=O)(=O)[O-])C(C)O.[Na+].[Na+].[Na+].[Na+].[Na+]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Colistimethate Sodium

2. Colistimethate, Disodium Salt

3. Colistin Sodium Methanesulfonate

4. Colistinmethanesulfonic Acid

2.2.2 Depositor-Supplied Synonyms

1. Sodium Colistin Methanesulfonate

2. Colistin Sulfomethate

3. Colimycin M

4. 12705-41-8

5. Colistinmethanesulfonic Acid

6. Sodium Colistimethate

7. Colistrimethate Sodium

8. Colymycin M

9. Coly-mycin M

10. Colimyscine

11. Colimicina

12. Coly-mycin Injectable

13. Colistin Sulfomethate Sodium

14. Coly-mycin M Parenteral

15. Sodium Colistinemethanesulfonate

16. Colistinemethanesulfonate Sodique

17. Pentasodium Colistinmethanesulfonate

18. Pentasodium;[2-[17-(1-hydroxyethyl)-22-[[2-[[3-hydroxy-2-[[2-(6-methyloctanoylamino)-4-(sulfonatomethylamino)butanoyl]amino]butanoyl]amino]-4-(sulfonatomethylamino)butanoyl]amino]-5,8-bis(2-methylpropyl)-3,6,9,12,15,18,23-heptaoxo-11,14-bis[2-(sulfonatomethylamino)ethyl]-1,4,7,10,13,16,19-heptazacyclotricos-2-yl]ethylamino]methanesulfonate

19. Einecs 232-516-9

20. Unii-xw0e5ys77g

21. Colistinmethanesulfonic Acid, Sodium Salt

22. 8068-37-9

23. Colistimethate Sodium [usan:usp:inn:ban]

24. Xw0e5ys77g

25. Unii-dl2r53p963

26. Dl2r53p963

27. Colistinmethanesulfonic Acid (van)

28. Nsc 756688

29. Sw222239-1

2.3 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₅₈H₁₀₅N₁₆Na₅O₂₈S₅
Molecular Weight	1749.8 g/mol
Hydrogen Bond Donor Count	18
Hydrogen Bond Acceptor Count	33
Rotatable Bond Count	39
Exact Mass	1748.5376240 g/mol
Monoisotopic Mass	1748.5376240 g/mol
Topological Polar Surface Area	749 Å²
Heavy Atom Count	112
Formal Charge	0
Complexity	3430
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	13
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	6

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Colistimethate sodium
PubMed Health	Colistimethate (Injection)
Drug Classes	Antibiotic
Drug Label	Colistimethate for Injection, USP is a sterile parenteral antibiotic product which, when reconstituted (see Reconstitution), is suitable for intramuscular or intravenous administration.Each vial contains colistimethate sodium or pentasodium colistinm...
Active Ingredient	Colistimethate sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 150mg base/vial
Market Status	Prescription
Company	Emcure Pharms; Fresenius Kabi Usa; Paddock; X Gen Pharms; Sagent Pharms

2 of 4
Drug Name	Coly-mycin m
Drug Label	Coly-Mycin M Parenteral (Colistimethate for Injection, USP) is a sterile parenteral antibiotic product which, when reconstituted (see Reconstitution), is suitable for intramuscular or intravenous administration.Each vial contains colistimethate sod...
Active Ingredient	Colistimethate sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 150mg base/vial
Market Status	Prescription
Company	Par Sterile Products

3 of 4
Drug Name	Colistimethate sodium
PubMed Health	Colistimethate (Injection)
Drug Classes	Antibiotic
Drug Label	Colistimethate for Injection, USP is a sterile parenteral antibiotic product which, when reconstituted (see Reconstitution), is suitable for intramuscular or intravenous administration.Each vial contains colistimethate sodium or pentasodium colistinm...
Active Ingredient	Colistimethate sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 150mg base/vial
Market Status	Prescription
Company	Emcure Pharms; Fresenius Kabi Usa; Paddock; X Gen Pharms; Sagent Pharms

4 of 4
Drug Name	Coly-mycin m
Drug Label	Coly-Mycin M Parenteral (Colistimethate for Injection, USP) is a sterile parenteral antibiotic product which, when reconstituted (see Reconstitution), is suitable for intramuscular or intravenous administration.Each vial contains colistimethate sod...
Active Ingredient	Colistimethate sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 150mg base/vial
Market Status	Prescription
Company	Par Sterile Products