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Rolitetracycline

Rolitetracycline structure

CAS No:
751-97-3
Formula:
C27H33N3O8
Chemical Name:
Rolitetracycline
Synonyms:
2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-,(4S,4aS,5aS,6S,12aS)-;2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-;2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-,[4S-(4α,4aα,5aα,6β,12aα)]-;(4S,4aS,5aS,6S,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-2-naphthacenecarboxamide;SQ 15659;4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-2-naphthacenecarboxamide;N-(Pyrrolidinomethyl)tetracycline;N-(1-Pyrrolidinylmethyl)tetracycline;Reverin;Rolitetracycline;Syntetrin;Velacycline;Abricycline;Tetraverin;Bristacin;Superciclin;Synotodecin;Transcycline;Pyrrolidinylmethyltetracycline;106408-39-3;107422-65-1;7433-04-7;801978-99-4;856650-20-9;878791-14-1
Categories:
Analytical Chemistry > Standard

Description

Rolitetracycline, a derivative of tetracycline, is a broad-spectrum antibiotic[1][2]. Rolitetracyclin has a role as a protein synthesis inhibitor, an antiprotozoal drug and a prodrug[3].

Rolitetracycline is a derivative of tetracycline in which the amide function is substituted with a pyrrolidinomethyl group. It has a role as an antibacterial drug, a protein synthesis inhibitor, an antiprotozoal drug and a prodrug. It is a member of tetracyclines and a tertiary alpha-hydroxy ketone.|A pyrrolidinylmethyl tetracycline.|A pyrrolidinylmethyl TETRACYCLINE.

Rolitetracycline Basic Attributes

Molecular Weight：

527.57

Exact Mass：

527.57

EC Number：

212-031-9

UNII：

GH9IW85221

NSC Number：

759177

DSSTox ID：

DTXSID7023568

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

171

XLogP3：

0.79860

Density：

1.542g/cm3

Melting Point：

160-165 °C (decomp)

Boiling Point：

824.37ºC at 760 mmHg

Flash Point：

452.363ºC

Refractive Index：

1.713

Water Solubility：

>20g/L(21 ºC)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

22-36/37/38

safety instructions：

26-36

RTECS Number：

QI9150000

Marks：

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H302-H315-H319-H335

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Symptoms of overdose include anorexia, nausea, diarrhoea, glossitis, dysphagia, enterocolitis and inflammatory lesions (with monilial overgrowth) in the anogenital region, skin reactions such as maculopapular and erythematous rashes, exfoliative dermatitis, photosensitivity, hypersensitivity reactions such as urticaria, angioneurotic oedema, anaphylaxis, anaphyl-actoid purpura, pericarditis, and exacerbation of systemic lupus erythematosus, benign intracranial hypertension in adults disappearing on discontinuation of the medicine, haematologic abnormalities such as haemolytic anaemia, thrombocytopenia, neutropenia, and eosinophilia. LD50=262 mg/kg (I.P. in rat).

Drug Information

Drug Indication：

Rolitetracycline is a broad-spectrum antibiotic used in cases needing high concentrations or when oral administration is impractical.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Mechanism of Action：

Rolitetracycline is a semisynthetic broad-spectrum tetracycline antibiotic used especially for parenteral administration in cases requiring high concentrations or when oral administration is impractical. Rolitetracycline passively diffuses through porin channels in the bacterial membrane and reversibly binds to the 30S ribosomal subunit, preventing binding of tRNA to the mRNA-ribosome complex, and thus interfering with protein synthesis.

MeSH Entry Terms：

Hydrochloride, Rolitetracycline

Rolitetracycline Use and Manufacturing

Rolitetracycline, launched in the late 1950s, was the first of the semi-synthetic tetracyclines.Rolitetracycline is formed by a Mannich condensation of formaldehyde and pyrrolidine with tetracycline. Rolitetracycline is a pro-drug of tetracycline, in which the pyrrolidine moiety improves bioavailability compared with tetracycline. Rolitetracycline has broad spectrum Gram positive activity in vivo, but pH instability limits use to parenteral administration. The intrinsic in vitro activity and SARs for this region of the tetracycline molecule have not been extensively investigated.

Computed Properties

Molecular Weight:527.6
XLogP3:-0.9
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:4
Exact Mass:527.22676502
Monoisotopic Mass:527.22676502
Topological Polar Surface Area:171
Heavy Atom Count:38
Complexity:1110
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes