pipacycline

pipacycline Structure
CAS No.
1110-80-1
Chemical Name:
pipacycline
Synonyms
Sieromicin;Pipacicline;Mepicycline;pipacycline;Tetrasolvina;(4S)-4β-Dimethylamino-1,4,4aβ,5,5aβ,6,11,12a-octahydro-3,6α,10,12,12aβ-pentahydroxy-N-[[4-(2-hydroxyethyl)-1-piperazinyl]methyl]-6-methyl-1,11-dioxo-2-naphthacenecarboxamide;2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-N-[[4-(2-hydroxyethyl)-1-piperazinyl]methyl]-6-methyl-1,11-dioxo-, (4S,4aS,5aS,6S,12aS)-
CBNumber:
CB7928471
Molecular Formula:
C29H38N4O9
Molecular Weight:
586.638
MOL File:
1110-80-1.mol
Modify Date:
2023/5/21 10:59:17

pipacycline Properties

alpha D20 -195° (c = 0.5); D20 -175° (c = 0.5 in methanol)
Boiling point 895.8±65.0 °C(Predicted)
Density 1.55±0.1 g/cm3(Predicted)
storage temp. Store at -20°C
solubility Soluble in DMSO
pka 4.50±1.00(Predicted)

SAFETY

Risk and Safety Statements

Toxicity LD50 i.v. in white mice: 188 mg/kg (Scalvini, Delmonte)

pipacycline Chemical Properties,Uses,Production

Uses

Pipacycline (mepicycline) is a semi-synthetic tetracycline formed by a Mannich condensation of formaldehyde and 4-hydroxyethylpiperazine with tetracycline. The introduction of the piperazine improves bioavailability, but Mannich bases are pro-drugs, converting back to the parent compound. Pipacycline is used commercially as a salt in combination with penicillin V for parenteral use (penimepicycline). The intrinsic in vitro activity and SARs for the amide region of the tetracycline molecule have not investigated extensively. Pipacycline has not been extensively cited in the literature.

Definition

ChEBI: Tetracycline in which a hydrogen attached to the amide nitrogen is substituted by a 4-[(2-hydroxyethyl)piperazin-1-yl]methyl group.

pipacycline Preparation Products And Raw materials

Raw materials

Preparation Products

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(4S)-4β-Dimethylamino-1,4,4aβ,5,5aβ,6,11,12a-octahydro-3,6α,10,12,12aβ-pentahydroxy-N-[[4-(2-hydroxyethyl)-1-piperazinyl]methyl]-6-methyl-1,11-dioxo-2-naphthacenecarboxamide Mepicycline Pipacicline Sieromicin Tetrasolvina pipacycline 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-N-[[4-(2-hydroxyethyl)-1-piperazinyl]methyl]-6-methyl-1,11-dioxo-, (4S,4aS,5aS,6S,12aS)- 1110-80-1 C29H38N4O9