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Rolitetracycline 751-97-3

Rolitetracycline 751-97-3

CAS No.: 751-97-3

Rolitetracycline is a antibiotic belonging to the tetracycline classthat may be given intravenously or intramuscularly i
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This product is for research use only, not for human use. We do not sell to patients.

Rolitetracycline is a antibiotic belonging to the tetracycline class that may be given intravenously or intramuscularly in serious bacterial infections when orally bioavailable administration is not practicable.


Physicochemical Properties


Molecular Formula C27H33N3O8
Molecular Weight 527.56622
Exact Mass 527.227
Elemental Analysis C, 61.47; H, 6.30; N, 7.96; O, 24.26
CAS # 751-97-3
Related CAS # 751-97-3 (free);7681-32-5 (nitrate anhydrous);
PubChem CID 54682938
Appearance Solid powder
Density 1.542g/cm3
Boiling Point 824.37ºC at 760 mmHg
Melting Point 163.5°C
Flash Point 452.363ºC
Index of Refraction 1.713
LogP 0.798
Hydrogen Bond Donor Count 6
Hydrogen Bond Acceptor Count 10
Rotatable Bond Count 4
Heavy Atom Count 38
Complexity 1110
Defined Atom Stereocenter Count 5
SMILES

C[C@@]1(O)C2=C(C(C3=C(O)[C@@]4(O)[C@H]([C@H](N(C)C)C(O)=C(C(NCN5CCCC5)=O)C4=O)C[C@@H]31)=O)C(O)=CC=C2

InChi Key IKQRPFTXKQQLJF-IAHYZSEUSA-N
InChi Code

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/h6-8,14-15,20,31-32,35,37-38H,4-5,9-12H2,1-3H3,(H,28,36)/t14-,15-,20-,26+,27-/m0/s1
Chemical Name

(4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-N-(pyrrolidin-1-ylmethyl)-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
Synonyms

Rolitetracycline; Reverin; Rolitetraciclina; Rolitetracyclinum; Solvocillin; Rolitetracycline Monohydrochloride.
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


Targets Tetracycline
References

[1]. SMITH L, ROLITETRACYCLINE, AN ANTIBIOTIC FOR PARENTERAL USE. (SYNTETRIN, VELACYCLINE). JAMA. 1964 Jan 11;187:141.

[2]. Structure–Activity Relationships in the Tetracycline Series. Advances in applied microbiology, 1970, 13:237-266.

[3]. Choudhary S, Kishore N. Unraveling the energetics and mode of the recognition of antibiotics tetracycline and rolitetracycline by bovine serum albumin. Chem Biol Drug Des. 2012 Nov;80(5):693-705. doi: 10.1111/cbdd.12009. Epub 2012 Aug 31. PubMed PMID: 22846623.

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

Solubility Data


Solubility (In Vitro) H2O : ~10 mg/mL (~18.95 mM)
DMSO : < 1 mg/mL
Ethanol : < 1 mg/mL
Solubility (In Vivo) Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300:Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)

Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.8955 mL 9.4774 mL 18.9548 mL
5 mM 0.3791 mL 1.8955 mL 3.7910 mL
10 mM 0.1895 mL 0.9477 mL 1.8955 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.