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Rolitetracycline

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Pharmaceutical drug

Pharmaceutical compound

Rolitetracycline
Clinical data


Other names	(2Z,4S,4aS,5aS,6S,12aS)-4-Dimethylamino-6,10,11,12a-tetrahydroxy-2-[hydroxy-(pyrrolidin-1-ylmethylamino)methylidene]-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione
ATC code	J01AA09 (WHO)
Identifiers
IUPAC name (2Z,4S,4aS,5aS,6S,12aS)-4-(Dimethylamino)-6,10,11,12a-tetrahydroxy-2-{hydroxy[(pyrrolidin-1-ylmethyl)amino]methylene}-6-methyl-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
CAS Number	751-97-3^Y
PubChemCID	54682938
DrugBank	DB01301^Y
ChemSpider	10469507^Y
UNII	GH9IW85221
KEGG	D02282^Y
ChEMBL	ChEMBL1214184^N
CompTox Dashboard(EPA)	DTXSID7023568
ECHA InfoCard	100.010.938
Chemical and physical data
Formula	C₂₇H₃₃N₃O₈
Molar mass	527.574 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(NCN1CCCC1)\C2=C(/O)[C@@H](N(C)C)[C@@H]3CC5C(=C(\O)[C@]3(O)C2=O)\C(=O)c4c(O)cccc4[C@@]5(C)O
InChI InChI=1S/C27H33N3O8/c1-26(37)13-7-6-8-16(31)17(13)21(32)18-14(26)11-15-20(29(2)3)22(33)19(24(35)27(15,38)23(18)34)25(36)28-12-30-9-4-5-10-30/h6-8,14-15,20,31,33-34,37-38H,4-5,9-12H2,1-3H3,(H,28,36)/t14?,15-,20-,26+,27-/m0/s1^Y Key:HMEYVGGHISAPJR-VQCPGFMQSA-N^Y
^NY (what is this?) (verify)

Rolitetracycline is atetracycline antibiotic.^[1] Tetracycline isN-Mannich base prodrug that is prepared fromtetracycline by condensation withpyrrolidine andformaldehyde to produce rolitetracycline.^[2] Rolitetracycline is used as an antibacterial drug, a protein synthesis inhibitor, an antiprotozoal drug and a prodrug.^[2]^[3]

^"Rolitetracycline".PubChem. National Library of Medicine. Retrieved8 June 2020.
^^a ^bPubChem."Rolitetracycline".pubchem.ncbi.nlm.nih.gov. Retrieved2022-07-29.
^Smith L (January 1964). "Rolitetracycline, an antibiotic for parenteral use. (syntetrin, velacycline)".JAMA.187 (2): 141.doi:10.1001/jama.1964.03060150065017.PMID 14066734.

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin^# Ribostamycin Kanamycin Amikacin^# Arbekacin Bekanamycin Dibekacin Tobramycin (+loteprednol) Spectinomycin^# Hygromycin B Totomycin Apramycin Nourseothricin
-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Micronomicin Plazomicin^# Isepamicin Verdamicin Astromicin
other	Butirosin

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Eravacycline Lymecycline Meclocycline^‡ Metacycline Minocycline Omadacycline Oxytetracycline Penimepicycline Rolitetracycline Sarecycline Tetracycline^#
Glycylcyclines	Tigecycline

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Macrolides	Boromycin Carbomycin Carrimycin Clarithromycin^# Dirithromycin Erythromycin^# Flurithromycin Josamycin Kitasamycin Midecamycin Miocamycin Nafithromycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Tildipirosin Tilmicosin Troleandomycin Tylosin Tylvalosin
Azalides	Azithromycin^# Gamithromycin Tulathromycin
Ketolides	Telithromycin^‡ Cethromycin Solithromycin^†
Lincosamides	Clindamycin^# Lincomycin Pirlimycin
Oxepanoprolinamides	Cresomycin Iboxamycin
Streptogramins	Pristinamycin (IA,IIA,IIB) NXL103 (Flopristin,Linopristin) Quinupristin/dalfopristin (Dalfopristin,Quinupristin) Streptogramin A Streptogramin B Virginiamycin (S1)

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