Structure via PubChem · Public domain (PubChem)
spiramycin
Sign in to saveAlso known as spiramycin I
Spiramycin is a macrolide antibiotic and antiparasitic. It is used to treat toxoplasmosis and various other infections of soft tissues.
Chemical data
- Formula
- C43H74N2O14
- Molecular weight
- 843.1 g/mol
- IUPAC name
- 2-[(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-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
- SMILES
- C[C@@H]1C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)O)N(C)C)O)CC=O)C)O[C@H]4CC[C@@H]([C@@H](O4)C)N(C)C
- InChIKey
- ACTOXUHEUCPTEW-KWBWCIJSSA-N
- XLogP
- 2.1
- Polar surface area
- 195 Ų
- H-bond donors
- 4
- H-bond acceptors
- 16
- Formal charge
- 0
via PubChem
Research
1,735 papers- Spiramycin renaissance.The Journal of antimicrobial chemotherapy · 1998
- [Spiramycin].Casopis lekaru ceskych · 1994
- SPIRAMYCIN.Canadian Medical Association journal · 1958
- SPIRAMYCIN.British medical journal · 1956
- Pharmacodynamics and pharmacokinetics of spiramycin and their clinical significance.Clinical pharmacokinetics · 1998
via PubMed
Wikidata facts
- Mass
- 842.514005
Show 4 more facts
- chemical formula
- C₄₃H₇₄N₂O₁₄
- canonical SMILES
- CC1CC=CC=CC(C(CC(C(C(C(CC(=O)O1)O)OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)CC=O)C)OC4CCC(C(O4)C)N(C)C
- isomeric SMILES
- CC1C/C=C/C=C/C(C(CC(C(C(C(CC(=O)O1)O)OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)CC=O)C)OC4CCC(C(O4)C)N(C)C
- Commons category
- Spiramycin
Sources (2)
via Wikidata · CC0
~5 min read
Article
7 sectionsContents
- Medical uses
- Available forms
- Pharmacology
- Pharmacodynamics
- Chemistry
- History
- References
{{Drugbox | Verifiedfields = changed | verifiedrevid = 477859140 | IUPAC_name = (4R,5S,6R,7R,9R,10R,11E,13E,16R)-10-{[(2R,5S,6R)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-9,16-dimethyl-5-methoxy-2-oxo-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-α-L-ribo-hexopyranosyl)-3-(dimethylamino)-α-D-glucopyranoside | image = Spiramycin I.svg | width = 350
| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = rx only | routes_of_administration = oral