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M1388

Sigma-Aldrich

Meclocycline sulfosalicylate salt

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About This Item

Empirical Formula (Hill Notation):
C22H21ClN2O8 · C7H6O6S
CAS Number:
73816-42-9
Molecular Weight:
695.05
EC Number:
277-614-2
MDL number:
MFCD00082372
UNSPSC Code:
51284010
PubChem Substance ID:
24896641
NACRES:
NA.85

color

yellow-green powder

solubility

methanol: 10 mL, clear, very dark yellow (200 mg + 10 mL MeOH)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

protein synthesis | interferes

SMILES string

OC(=O)c1cc(ccc1O)S(O)(=O)=O.CN(C)[C@H]2[C@@H]3[C@@H](O)C4C(=C)c5c(Cl)ccc(O)c5C(=O)C4=C(O)[C@]3(O)C(=O)C(C(N)=O)=C2O

InChI

1S/C22H21ClN2O8.C7H6O6S/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30;8-6-2-1-4(14(11,12)13)3-5(6)7(9)10/h4-5,10,14-15,17,26,28-30,33H,1H2,2-3H3,(H2,24,32);1-3,8H,(H,9,10)(H,11,12,13)/t10?,14-,15+,17+,22+;/m1./s1

InChI key

FYSVKUUNXYGFLA-FRGFDCQGSA-N

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General description

Chemical structure: tetracycline

Application

Meclocycline is a tetracycline antibiotic. It is used topically for skin infections[1]. It is used to study papulopustular acne and to study the effectiveness of oral versus topical administration[2][3].

Biochem/physiol Actions

Meclocycline sulfosalicylate prevents bacterial protein synthesis through 30S ribosome-mediated chain elongation and blocks amino-acyl tRNA A-site binding.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
050H0682

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J V Hirschmann
Archives of dermatology, 124(11), 1691-1700 (1988-11-01)
Topical antibiotics are safe and effective in certain conditions, primarily acne, rosacea, and nasal carriage of Staphylococcus aureus. They are useful in impetigo only when it is of limited extent. Their efficacy in other pyodermas is unclear, although mupirocin is
The use of antibiotics in acne therapy: oral or topical administration?
E A Eady et al.
The Journal of antimicrobial chemotherapy, 10(2), 89-115 (1982-08-01)
R S Stern et al.
Archives of dermatology, 120(12), 1571-1578 (1984-12-01)
We used cost-effectiveness analysis to compare the costs, risks, and benefits of two strategies for clearing papulopustular acne; topical therapy alone as initial therapy or a combination of systemic antibiotics and topical agents used at the first visit. Patients treated

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