1035979-44-2

Basic information

• Product Name: (4S,4aS,5aR,12aS)-4-(DiMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-7-[(MethoxyMethylaMino)Methyl]-1,11-dioxo-2-naphthacenecarboxaMide hydrochloride
• Synonyms: (4S,4aS,5aR,12aS)-4-(DiMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-7-[(MethoxyMethylaMino)Methyl]-1,11-dioxo-2-naphthacenecarboxaMide hydrochloride;P005672 HCl;P005672 (hydrochloride);Sarecycline (hydrochloride);Sarecycline;4S,4aS,5aR,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-7-[(methoxymethylamino)methyl]-1,11-dioxo-2-naphthacenecarboxamide hydrochloride P005672 HCl;Sarecycline HCl;(4S,4AS,5aR,12aS)-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-((methoxy(methyl)amino)methyl)-
• CAS NO: 1035979-44-2
• Molecular Formula: C₂₄H₂₉N₃O₈*ClH
• Molecular Weight: 523.9633
• Mol File: 1035979-44-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4S,4aS,5aR,12aS)-4-(DiMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-7-[(MethoxyMethylaMino)Methyl]-1,11-dioxo-2-naphthacenecarboxaMide hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,4aS,5aR,12aS)-4-(DiMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-7-[(MethoxyMethylaMino)Methyl]-1,11-dioxo-2-naphthacenecarboxaMide hydrochloride(1035979-44-2)
• EPA Substance Registry System: (4S,4aS,5aR,12aS)-4-(DiMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-7-[(MethoxyMethylaMino)Methyl]-1,11-dioxo-2-naphthacenecarboxaMide hydrochloride(1035979-44-2)

Safety Data

• Hazardous Substances Data: 1035979-44-2(Hazardous Substances Data)

Usage

Uses

Sarecycline Hydrochloride is a substituted tetracycline compound used for treatment of bacterial infections and neoplasms.

Synthetic route

C2HF3O2*C24H29N3O8 (1035978-85-8) → (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide mono hydrochloride (1035979-44-2)

Conditions	Yield
With hydrogenchloride In methanol

(4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide (1035654-66-0) → (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide mono hydrochloride (1035979-44-2)

Conditions	Yield
With hydrogenchloride In ethanol; water at 5℃; pH=1.3 - 1.6;
With hydrogenchloride In ethanol pH=1.3 - 1.6;

7-formylsancycline (1035655-10-7) → (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide mono hydrochloride (1035979-44-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium cyanoborohydride / N,N-dimethyl acetamide / 0.25 h / 20 °C / Inert atmosphere 2: hydrogenchloride / ethanol; water / 5 °C / pH 1.3 - 1.6 View Scheme

Upstream product

• 1035978-85-8 C₂HF₃O₂*C₂₄H₂₉N₃O₈ 
• 1035655-10-7 7-formylsancycline 
• 1035654-66-0 (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide 

Relevant articles and documents

METHODS OF USING (4S,4AS,5AR,12AS)-4-DIMETHYLAMINO-3,10,12,12A-TETRAHYDROXY-7-[(METHOXY(METHYL)AMINO)-METHYL]-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-NAPHTHACENE-2-CARBOXYLIC ACID AMIDE

A method of treating a bacterial infection, e.g., a bacterial infection with methicillin resistant Staphylococcus aureus, Helicobacter pylori, Chlamydia trachomatis, or Chlamydia pneumonia, comprising administering to a subject (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide or a pharmaceutically acceptable salt thereof is disclosed. More specifically, a method of treating a bacterial infection comprising administering to a subject crystalline mono hydrochloride salt, crystalline mono mesylate salt or crystalline mono sulfate salt of (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide is disclosed.

SUBSTITUTED TETRACYCLINE COMPOUNDS FOR TREATMENT OF INFLAMMATORY SKIN DISORDERS

Methods and compositions for the treatment of skin disorders (e.g., acne, rosacea) are described.