126544-47-6 Usage
Description
Ciclesonide, also known as Alvesco, is a glucocorticoid prodrug that is converted into its active form, des-ciclesonide, through hydrolysis. It is a white solid with minimal oral bioavailability due to extensive metabolism, primarily by CYP3A4. Ciclesonide is used as an inhaled corticosteroid (ICS) for the prophylactic treatment of persistent asthma, offering a longer duration of action and lower systemic exposure compared to other ICS drugs.
Uses
Used in Pharmaceutical Industry:
Ciclesonide is used as an inhaled corticosteroid for the prophylactic treatment of persistent asthma. It acts as a potent glucocorticoid receptor (GR) agonist, providing anti-inflammatory effects to manage chronic asthma symptoms. The key differentiators for ciclesonide include its longer duration of action and lower systemic exposure, which may reduce the potential for side effects associated with long-term use of high-dose ICS.
Used in Allergy Treatment:
Ciclesonide is also used as a glucocorticoid microemulsion nasal preparation to inhibit allergic rhinitis. By modulating the glucocorticoid receptor, it helps to alleviate the symptoms of allergic reactions in the nasal passages.
Chemical Production:
Ciclesonide is chemically produced via a semi-synthesis starting from 16-α-hydroxyprednisolone. The process involves converting it to a triisobutyryl ester intermediate with isobutyric anhydride, followed by a reaction with cyclohexane carboxaldehyde and hydrochloric acid in dioxane. The resulting cyclic ketal is a mixture of diastereomers, which is then subjected to HPLC and fractional crystallization to produce ciclesonide.
Brand Name:
Alvesco (Dynamit Nobel GmbH) is the brand name under which Ciclesonide is marketed.
Originator
Recordati
Espana (Spain)
Synthesis
Two separate approaches to the
syntheses of the chiral ciclesonide have been described in the
patent literature. The first route involves a chiral resolution
step and the second approach highlights a stereoselective
trans acetalization approach. The first synthesis of
ciclesonide started by reacting (11β,16α)-11,
16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione (1) with
isobutyric anhydride to make the tri-isobutyl ester in 87%
yield. Reaction of the tri-ester with cyclohexane carboxaldehyde
in the presence of HCl and 70% perchloric acid gave
the cyclohexane acetal 3, which was then separated into the
desired isomer ciclesonide (I) by HPLC or recrystallization.
Check Digit Verification of cas no
The CAS Registry Mumber 126544-47-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,6,5,4 and 4 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 126544-47:
(8*1)+(7*2)+(6*6)+(5*5)+(4*4)+(3*4)+(2*4)+(1*7)=126
126 % 10 = 6
So 126544-47-6 is a valid CAS Registry Number.
InChI:InChI=1/C32H44O7/c1-18(2)28(36)37-17-25(35)32-26(38-29(39-32)19-8-6-5-7-9-19)15-23-22-11-10-20-14-21(33)12-13-30(20,3)27(22)24(34)16-31(23,32)4/h12-14,18-19,22-24,26-27,29,34H,5-11,15-17H2,1-4H3/t22-,23-,24-,26+,27+,29+,30-,31-,32+/m0/s1
126544-47-6Relevant articles and documents
Preparation method of ciclesonide
-
, (2021/08/07)
The invention discloses a preparation method of ciclesonide. The preparation method comprises the following steps: aldolization reaction, primary purification, hydrolysis reaction, esterification reaction and secondary purification. Aldolization reaction:
Pregnane derivatives 16, 17 - acetal (ketone) preparation method
-
Paragraph 0043-0045, (2017/08/31)
Disclosed is a method for preparing a pregnane derivative 16,17-acetal (ketal) compound shown in the general formula I, the method comprising the step of reacting a compound of a general formula II with a compound of a general formula III or a general formula IV in the presence of boron trifluoride, wherein the dotted line between site 1 and site 2 denotes a saturated or unsaturated bond; R is hydroxyl, halogen or -OCOR7, wherein R7 is a C1-C12 linear chain or branched alkyl, a C3-C10 cycloalkyl, a C2-C8 alkenyl or a C2-C8 alkynyl; R1 and R2 are each hydrogen, a C1-C12 linear chain or branched alkyl, a C3-C10 cycloalkyl, a C2-C8 alkenyl or a C2-C8 alkynyl, or R1, R2 and the carbon to which they are connected form a C3-C10 cycloalkyl together, with the provision that R1 and R2 are not hydrogen simultaneously; R3 is hydrogen or -OCOR8, wherein R8 is a C1-C12 linear chain or branched alkyl, or a C3-C10 cycloalkyl; R4 is hydrogen, fluorine or chlorine; R5 is hydrogen, fluorine, chlorine or methyl; and R6 is a C1-C12 linear chain or branched alkyl. Compared with current processes, the method causes little pollution to the environment, has relatively mild reaction conditions, ease of control, reduced energy consumption and low production costs.
NOVEL METHOD FOR MANUFACTURING OF CICLESONIDE
-
, (2013/09/12)
The invention relates to a process for preparing ciclesonide in epimerically pure form, a corticosteroid of formula 1: Ciclesonide is used for the treatment of respiratory complaints.
