81846-19-7 Usage
Description
REMODULIN, also known as Treprostinil, is a synthetic analog of Prostacyclin (P839060). It is a medication that possesses antihypertensive properties and is primarily used to treat pulmonary arterial hypertension (PAH).
Uses
Used in Pharmaceutical Industry:
REMODULIN is used as an antihypertensive medication for the treatment of pulmonary arterial hypertension (PAH). It helps to improve blood flow and reduce the pressure in the pulmonary arteries, providing relief to patients suffering from this condition.
Pharmacokinetics
Treprostinil is
rapidly absorbed from the subcutaneous site of infusion, with an almost 100% bioavailability and a mean half-life of 85
minutes (34 minutes for the IV infusion). The IV solution must be diluted with normal saline or sterile water before
starting the infusion. Unlike epoprostenol, treprostinil is stable at room temperature for up to 5 years, with vasodilation
action lasting from 4 to 6 hours, compared with the short, 2- to 3-minute action for epoprostenol. Because of its long
life in the body, it can be administered under the skin with a microinfusion subcutaneous infusion pump rather than into
the bloodstream and, thus, without hospitalization, as contrasted with the central IV infusion of epoprostenol.
Clinical Use
Treprostinil is a synthetic, stable form of prostacyclin for the treatment for advanced pulmonary
hypertension with NYHA class III or IV symptoms as well as for late-stage peripheral vascular disease (PVD). Its sodium
salt injectable form is administered either as a continuous subcutaneous infusion directly into the skin or, if the
subcutaneous infusion is not tolerated, as a continuous IV infusion without an implanted catheter.
Side effects
Side effects include jaw pain, headaches, nausea, diarrhea, flushing, and localized pain at the delivery site under the
skin. This pain has been reported as slight to severe irritation. Patients using the drug seem to ex-perience
improvement in their condition, including decreased fatigue, decreased shortness of breath, and decreased pulmonary
artery pressures, as well as overall improvement in quality of life.
Check Digit Verification of cas no
The CAS Registry Mumber 81846-19-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,1,8,4 and 6 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 81846-19:
(7*8)+(6*1)+(5*8)+(4*4)+(3*6)+(2*1)+(1*9)=147
147 % 10 = 7
So 81846-19-7 is a valid CAS Registry Number.
InChI:InChI=1/C23H34O5/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27)/t16-,17-,18+,19-,21+/m0/s1
81846-19-7Relevant articles and documents
EFFICIENT CRYSTALLIZATION PROCESS FOR PREPARING ULTRAPURE TREPROSTINIL AND CRYSTAL PREPARED THEREFROM
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Paragraph 0083-0084, (2021/06/26)
There is provided a crystalline Form I of anhydrous Treprostinil and processes for the preparation thereof. The crystalline Form I of anhydrous Treprostnil is a stable crystalline form, which can provide steady physicochemical properties for pharmaceutical formulations, and is advantageous widely and safety used in storage, shipment, and handling for commercially considerations.
Synthesis of treprostinil: Key claisen rearrangement and catalytic pauson-khand reactions in continuous flow
García-Lacuna, Jorge,Domínguez, Gema,Blanco-Urgoiti, Jaime,Pérez-Castells, Javier
, p. 9489 - 9501 (2019/11/14)
A new synthesis of treprostinil is described using a plug flow reactor in two of the key steps. First, a Claisen rearrangement reaction is described in scaled flow at multigram amounts. Yields and selectivity of this step are sharply improved compared to those from previous syntheses. Second, the key Pauson-Khand reaction in flow is described under catalytic conditions with 5 mol% of cobalt carbonyl and only 3 equiv. of CO. Scaling up of this reaction safely ensures a good yield of an advanced intermediate which is transformed into treprostinil in three steps. Other improvements are the introduction of the carboxymethyl chain into the phenol from the beginning to reduce the protection-deprotection steps. The synthesis is completed in 14% global yield after 12 linear steps from (S)-epichlorhydrin.
Process for Preparing Treprostinil and Intermediate Therefor
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, (2018/02/21)
The present invention relates to a synthesis method of high-purity treprostinil, and an intermediate for the same. According to the synthesis method of the present invention, high-purity treprostinil can be synthesized in an economical and efficient manner by using intramolecular Friedel-Crafts allylic alkylation. Accordingly, the synthesis method of the present invention may be effectively used for commercial mass-production of treprostinil.COPYRIGHT KIPO 2017