gamithromycin

CHEBI:195437 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A macrolide antibiotic with formula C40H76N2O12. It is used for the treatment of of bovine respiratory disease caused by Mannheimia haemolytica, Pasteurella multocida, Histophilus somni and Mycoplasma bovis in beef and non-lactating dairy cattle. The compound is also licensed in Europe for the treatment of footrot in sheep caused by Dichelobacter nodosus and Fusobacterium nodosus. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

macrolide antibioticARO:0000000

Strictly broader compounds or drug classes this molecule belongs to.

macrolide antibiotic CHEBI:25105
Label unavailable CHEBI:63367
macrolide antibiotic ARO:0000000

Chemical structure

Computed structure properties
Molecular formula	C40H76N2O12
Charge	0
Average mass	777.05 Da
Monoisotopic mass	776.53983 Da
Source	ChEBI
InChIKey	VWAMTBXLZPEDQO-UZSBJOJWSA-N

SMILES

CCCN1C[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@H]1C

InChI

InChI=1S/C40H76N2O12/c1-15-17-42-21-22(3)33(44)40(11,48)29(16-2)52-36(46)26(7)32(53-30-20-39(10,49-14)34(45)27(8)51-30)25(6)35(38(9,47)19-23(42)4)54-37-31(43)28(41(12)13)18-24(5)50-37/h22-35,37,43-45,47-48H,15-21H2,1-14H3/t22-,23+,24+,25-,26+,27-,28-,29+,30-,31+,32-,33+,34-,35+,37-,38+,39+,40+/m0/s1

Also called

Zactran (BRAND_NAME)— chebi
gamithromycinum (INN)— chebi
gamitromicina (INN)— chebi
(2R,3S,4R,5S,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-15-oxo-7-propyl-11-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-1-oxa-7-azacyclopentadecan-13-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranoside (EXACT_SYNONYM)— chebi
(2R,3S,4R,5S,8R,10R,11R,12S,13S,14R)-13-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-7-propyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-7-azacyclopentadecan-15-one (EXACT_SYNONYM)— chebi
ML 1709460 (EXACT_SYNONYM)— chebi
ML-1,709,460 (EXACT_SYNONYM)— chebi
ML-1709460 (EXACT_SYNONYM)— chebi
ML-460 (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antimicrobial agent CHEBI:33281
antibacterial drug CHEBI:36047

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3007761`	gamithromycin	`antibioticmech:aro-f01e55d3f1`	2026-08-30
CHEBI	`CHEBI:195437`	gamithromycin	`antibioticmech:chebi-f6ea5129bc`	2026-08-30

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:48001 (protein synthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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